bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis of 17B‐hydroxy‐[14α, 15α‐ 3H] estra‐4,9‐dien‐3‐one
Authors: Römer J. , Teich A. , Droescher P. , Teichmüller G. 
Published: October 2006

AbstractStarting with catalytic tritiation of 3‐methoxy‐estra‐1,3,5(10),8,14‐pentaen‐17B‐01 (1) the preparation of 17B‐hydroxy‐[14α,15α ‐3H] estra‐4,9‐dien‐3‐one (5) is described. The dienone (5) was obtained with a specific activity of 400 GBq/mmol and a radiochemical purity better than 96%. The intermediate unconjugated ketone (3) and also the dienone (5) were found to be very sensitive to self‐radiolysis.
Synthesis, purification and stability in solution of dithiobiuret‐2,4‐ 35S
Authors: Porter William R. , Williams Kevin D. , Peterson Richard E. 
Published: October 2006

Abstract2,4‐Dithiobiuret (dithioimidodicarbonic diamide) can be labelled with 35S by isotopic exchange with hydrogen sulfide‐ 35S in boiling 0.01N hydrochloric acid. The product obtained by crystallization from the reaction medium contains more than 93% of the radioactivity as 2,4‐dithiobiuret and less than 3% as thiuret (3,5‐diimino‐1,2,4‐dithiazoline). Up to 40% of the initial radioactivity can be recovered as solid products. Solutions containing dithiobiuret must be stored under refrigeration to prevent decomposition to thiuret, monothiobiuret, and other products. Solutions prepared in this way are stable for 8 days. Dithiobiuret may be separated from thiuret, monothiobiuret, biuret and unidentified decomposition products by thin‐layer chromatography on silica gel.
18O‐labeled nucleosides 3. Preparation and mass spectrometric evaluation of 18O2‐labeled ara‐C and ara‐U
Authors: Schubert Ernst M. , Schram Karl H. 
Published: October 2006

AbstractA facile method for the preparation of 18O labeled ara‐C and ara‐U is described. The method provides a means of incorporating 18O specifically at the 2‐position of the nucleobase. The site and level of label was established using mass spectrometry.
Synthesis of carbon‐13 labeled 5‐(diethylphosphono)‐2‐pentanone ethylene ketal, a reagent for synthesis of multi C‐13 labeled steroids
Authors: Degraw Joseph I. , Christie Pamela H. , Cairns Thomas 
Published: October 2006

AbstractAlkylation of ethyl acetoacetate‐13C4 with ethylene oxide and ethylene oxide‐13C2 afforded 2‐acetylbutyrolactone‐13C4 (4a) and the hexalabeled form (4b), respectively. Treatment of the lactone with an excess of 48% hydrobromic acid effected decarboxylation with bromide displacement to yield 5‐bromo‐2‐pentanone labeled with 3 or 5 carbon‐13 atoms (5). The bromo ketone was converted to the ethylene ketal with ethylene glycol and p‐toluenesulfonic acid catalysis. Displacement of the bromide by sodio diethyl phosphite gave the required ethylene ketals of 5‐(diethylphosphono)‐2‐pentanone (7). A convenient process for preparation of ethylene‐13C2 oxide from acetic‐13C2 acid is also described.
Synthesis of encainide‐13C hydrochloride from 2‐nitrobenzaldehyde‐formyl‐13C
Authors: Johnson Porter C. , Covington Robert R. 
Published: October 2006

AbstractA tacile synthesis of 2‐nitrobenzaldehyde‐formyl‐13C was developed. This compound was converted to the labelled antiarrhythmic agent, encainide‐13C hydrochloride, 4‐methoxy‐N‐[2‐[2‐(1‐methyl‐2‐piperidinyl)ethyl‐1‐13C]phenyl]benzamide hydrochloride.
Synthesis of 2‐naphthalene‐d7‐sulfonic acid
Authors: Sniegoski Lorna T. , Edward White V. , Konash Pamela L. 
Published: October 2006

Abstract2‐Naphthalene‐d7‐sulfonic acid, required as an internal standard for the analysis of organic compounds in water by gas chromatography/mass spectrometry, was synthesized in one step from commercially available naphthalene‐d8 and sulfuric acid‐d2. A high‐performance liquid chromatographic method was developed to separate 1‐ and 2‐naphthalene‐d7‐sulfonic acids. The electron impact mass spectrum and isotopic purity of the 2‐naphthalene‐d7‐sulfonic acid were determined.
Preparation of N(1‐ethyl‐2‐pyrrolidyl‐methyl)2‐methoxy‐4‐iodo‐125I‐ 5‐ethyl sulfonyl benzamide: A radioligand for the radioimmunoassay of sulpiride‐related compounds
Authors: Cardoso Maria Teresa , Pradelles Philippe 
Published: October 2006

AbstractWe describe the preparation of 125I labelling with a higher specific radioactivity of N(1‐ethyl ‐2‐pyrrolidyl‐methyl)2‐ methoxy ‐5‐ethyl sulfonyl benzamide, a potent biological analogue for sulpiride. The incorporation of iodine in the molecule was achieved by the substitution of aromatic amino groups via the diazo compound. Binding and immunological parameters of iodinated and tritiated tracers were compared.
A rapid synthesis of 2‐deoxy‐2‐fluoro‐d‐glucose from xenon difluoride suitable for labelling with 18F
Authors: Shiue Chyng‐Yann , K.‐C.  , Wolf Alfred P. 
Published: October 2006

AbstractA rapid synthesis of 2‐deoxy‐2‐fluoro‐D‐glucose (3) from xenon difluoride is described. Reaction of 3,4,6‐tri‐O‐acetyl‐D‐glucal (1) with xenon difluoride in ethyl ether in the presence of BF3·OEt2 for 20 minutes gave 2‐deoxy‐2‐fluoro‐ 3,4,6‐tri‐O‐acetyl‐D‐glucopyranosyl fluoride (2) in 70‐80% chemical yield. Hydrolysis of 2 with 2 N HCl gave 2‐deoxy‐2‐fluoro‐D‐glucose (3) in 50% overall chemical yield in a synthesis time of 60 minutes. Preliminary results indicate that this method can be used to synthesize 2‐deoxy‐2‐ [18F] fluoro‐D‐glucose.
Preparation of carbon‐14 labelled ethyl 2‐(P‐chlorophenoxy)‐2‐methyl propionate (CLofibrate; atromid‐S); clofibric acid and clofibric amide
Authors: Burns J. 
Published: October 2006

AbstractThe preparation of [14C] Ethyl 2‐(p‐chlorophenoxy)‐2‐methyl propionate (Atromid‐S; clofibrate) with the label separately located in three different positions is described, together with purification procedures employed. From each of the three labeled products, clofibric acid (CPIB acid;ICI 7132) has been prepared by hydrolysis. The labeled amide has also been synthesized.
1,3‐dihydroxybenzene‐2‐13C: Its preparation and reaction with chlorine and bromine in aqueous solution
Authors: Boyce Scott D. , Barefoot Aldos C. , Hornig James F. 
Published: October 2006

Abstract1,3‐cyclohexanedione‐2‐13C was prepared by intramolecular Claisen condensation of methyl 5‐oxohexanote‐6‐13C with sodium methoxide. Formation of the ketoester starting material involved treatment of a mixed dicarboxylic anhydride with an isotopicallylabelled Grignard reagent, methyl‐13C magnesium iodide. Dehydrogenation of carbon‐13 labelled cyclohexanedione over a palladium/carbon catalyst produced 1,3‐dihydroxybenzene‐2‐13C. Chlorination and bromination of dihydroxybenzene in aqueous solution yielded isotopically‐labelled chloroform and bromoform, each having enriched carbon‐13 contents equivalent to that of the organic substrate.
An efficient synthesis of ethyne‐1‐13C
Authors: Colborn Robert E. , Vollhardt K. Peter C. 
Published: October 2006

AbstractA synthesis of the title compound from 13CO2 is described. The final step utilizes lithium hexamethyldisilazide as a base in the double dehydrobromination of 1,2‐dibromoethane‐1‐13C. Some alternative procedures are discussed.
N‐succinimidyl propionate: Characterisation and optimum conditions for use as a tritium labelling reagent for proteins
Authors: Tang Yui S , Davis Ann‐Marie , Kitcher J Philip 
Published: October 2006

AbstractN‐Succinimidyl propionate [NSP] was synthesised and characterised as a pale yellow waxy solid. Rates of hydrolysis in buffers range pH 5–9 were determined. Optimum conditions for reaction with lysine were within the range pH 7 to 8. A protein, wheat germ agglutinin was labelled at pH 7.5 at room temperature for two hours. Rates of reaction of other substrates under these conditions were investigated.
[14C]Senecionine and [14C]isosenecionine from the pyrrolizidine alkaloid retrorsine
Authors: Mattocks A. Robin 
Published: October 2006

AbstractRetrorsine (1) has been oxidized to a mixture of two epimeric cyclic keto esters (2) which, [14C]methylmagnesium iodide gave [18‐14C]senecionine (3a) and [18‐14C] isosenecionine (3d).
Syntheses of 1‐dodecyl‐d25 phosphate
Authors: Sniegoski Lorna T. , White Edward 
Published: October 2006

Abstract1‐Dodecyl‐d25 phosphate was prepared from commercially available 1‐dodecanol‐d26. The 1‐dodecanol‐d26 reacted with diphenyl phosphorochloridate to produce 1‐dodecyl‐d25 diphenyl phosphate, which was reduced with hydrogen in the presence of Adams catalyst to give a 58.9 percent yield of 1‐dodecyl‐d25 phosphate with 99.4 atom percent deuterium.
Synthesis of 195Au, 32P and 35S‐labelled auranofin, A novel orally effective gold antiarthritic drug
Authors: Hill David T. , Sutton Blaine M. , Levinson Sidney H. , Meier Joseph , Kline Smith 
Published: October 2006

AbstractAuranofin (1), a phosphine gold(I) thiolate antiarthritic agent effective on oral administration, was labelled separately with 195Au, 32P and 35S. 195Au‐labelled auranofin 19 was made from H195AuCl4.3H20 via the intermediate chloro(triethylphosphine)gold‐195Au (18). Auranofin ‐35S (23) was prepared using thiourea‐35S. The synthetic routes for 19 and 23 were similar to those used for unlabelled 1. However, auranofin‐32p (28) was made by the novel, direct coupling of the 1: complex (2,3,4,6‐tetraO‐acetyl‐l‐thio‐β‐D‐glucopyranosato‐S)gold (27) with 32p(C2H5)3 (26) synthesized from 32PCl3 (24). The labelled compounds were used in pharmacokinetic, tissue distribution and metabolism studies.
D‐glucose derivatives labelled with 75,77Br and 123I
Authors: Kloster Gerd , Laufer Peter , Stöcklin Gerhard 
Published: October 2006

AbstractSynthetic routes to D‐glucose derivatives labelled with either the positron emitter 75Br (T1/2 = 1.6 hr) or the single photon emitters 77Br (T1/2 = 56 hr) and 123I (T1/2 = 13.3 hr) in positions 2 or 3 were investigated in order to prepare useful tracers for glucose utilization studies in brain and heart.3‐Deoxy‐3‐iodo‐D‐glucose and 3‐deoxy‐3‐bromo‐D‐glucose were prepared from 1,2:5,6‐di‐isopropylidene‐D‐allose via its triflate in 10‐20 % radiochemical yield.2‐Deoxy‐2‐iodo‐D‐glucose and 2‐deoxy‐2‐bromo‐D‐glucose could not be prepared by the routes presented in this publication. On the route to these compounds, some intermediates of possible use as tracers for glucose utilization were prepared, namely the methyl glucosides methyl 2‐deoxy2‐iodo‐β‐D‐glucopyranoside (MIDG) and methyl 2‐deoxy‐2‐bromo‐β‐D‐glucopyranoside (MBDG) and the acetylated methyl glucosides methyl 3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐iodo‐β‐D‐glucopyranoside (MTIG) and methyl 3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐bromo‐β‐D‐glucopyranoside (MTBG). Radiochemical yields from 3,4,6‐tri‐O‐acetyl‐D‐glucal, halide ion and dichloramin T were 35 % for MTBG, 40 % for MTIG, 15 % for MBDG and 20 % for MIDG. Preparation times were less than 2 hours.
Quality control procedures in the preparation of 2‐deoxy‐D‐[1‐11C] glucose radiopharmaceutical
Authors: Vora Manhar M. , Boothe Thomas E. , Finn Ronald D. , Smith Patricia M. , Gilson Albert J. 
Published: October 2006

AbstractPreparation and quality control of 2‐deoxy‐D‐[1‐11C] glucose (11C‐2DG, 1) have been accomplished by a combination of cation‐exchange and high performance liquid chromatography (HPLC) to give the radiopharmaceutical in greater than 99% radiochemical purity and an overall 25‐35% radiochemical yield in 45‐50 min. Quality control procedures utilizing GC and HPLC have been developed to determine not only chemical and radiochemical purity of the final product, but also to examine the reactants used and the products formed during the preparation of 1.
Tritium labelling of enkephalin analogs : Tyr‐D‐Ala‐Gly‐NH‐CH(CH3)‐CH2‐CH(CH3)2 (trimu 4), Tyr‐D‐Ser‐Gly‐Phe‐Leu‐Thr (DSLET), Tyr‐D‐Thr‐Gly‐Phe‐Leu‐Thr (DTLET), μ and δ opiate‐receptors specific ligands
Authors: Gacel G. , Dodey P. , Roques B. P. , Morgat J. L. , Roy J. , Fromageot P. 
Published: October 2006

AbstractUnambiguous biochemical characterization of the different opiate receptors (i.e., μ and δ) imperatively requires fully specific and radiolabelled ligands. Therefore, in this paper, we report the synthesis of the 3,5‐dibromotyrosyl precursors of three highly selective peptides : Tyr‐D‐Ala‐Gly‐NH‐CH(CH3)‐CH2‐CH(CH3)2, TRIMU 4 (μ) Tyr‐D‐Ser‐Gly‐Phe‐Leu‐Thr, DSLET (δ) and Tyr‐D‐Thr‐Gly‐Phe‐Leu‐Thr, DTLET (δ). Reductive tritiation by exchange with 3H2 leads to the labelled enkephalins analogs in high yields and with specific activities between 45 to 60 Ci/mmole.
Preparation and purification of 77Br‐labelled p‐bromospiroperidol suitable for in vivo dopamine receptor studies
Authors: Dejesus Onofre T. , Friedman Arnold M. , Prasad Anita , Revenaugh James R. 
Published: October 2006

AbstractAn efficient and reliable method of preparing 77Br‐p‐bromo spiroperidol suitable for labelling dopamine receptors in vivo has been developed. This synthesis involves the reaction of 77Br−, H2O2, and spiroperidol in glacial acetic acid. The purity of the product was assured by the use of two column reverse phase high performance liquid chromatography. Radio‐chemical yields were in the range of 80–90%, while specific activities of 80–140 Ci/mmole were obtained at the end of the synthesis.
Synthesis of deuterium labelled perphenazine
Authors: Hawes E. M. , Gurnsey T. S. , Shetty H. U. , Midha K. K. 
Published: October 2006

AbstractProcedures for the preparation of perphenazine‐d2, ‐d4, and ‐d6, and N‐deshydroxyethylperphenazine‐d4 and ‐d6 are described. Deuterium was introduced in the propylpiperazine side chain by treatment of the appropriate ester or imide with lithium aluminum deuteride. The γ‐carbon of the propyl group was labelled with two deuterium atoms by reduction of 2‐chloro‐10‐(2‐methoxycarbonylethyl)‐10H‐phenothiazine, while four deuterium atoms were incorporated into the piperazine ring by reduction of 2‐chloro‐10‐[3‐(3,5‐dioxo‐1‐piperazinyl)‐propyl]‐10H‐phenothiazine.
Synthesis of 14C‐labeled 5‐[1‐hydroxy‐2‐[2‐(o‐methoxyphenoxy) ethylamino] ethyl]‐2‐methylbenzenesulfonamide hydrochloride (YM‐09538)
Authors: Arima Hideki , Tamazawa Kazuharu 
Published: October 2006

AbstractPreparation of the title compound, a novel antihypertensive agent, is described. The labeled material with a specific activity of 4.76 mCi/mmol was synthesized in a 50.6% radiochemical yield from [U‐14C]ethylene oxide via a process of six steps.
The synthesis of (3H)‐xylamine, an irreversible inhibitor of norepinephrine uptake
Authors: Ransom R. W. , Kammerer R. C. , Cho A. K. 
Published: October 2006

AbstractXylamine [N‐(2‐chloroethyl)‐N‐ethyl‐2‐methylbenzylamine], an irreversible inhibitor of neuronal norepinephrine uptake, has been synthesized with tritium incorporated in the aromatic nucleus. Initially, 2‐methylbenzyl bromide was nonselectively mono‐brominated on the ring and the resulting isomeric products were condensed with 2‐(ethylamino)ethanol. Unequivocal identification of the products of each reaction was provided by mass spectral analysis. A mixture of mono‐bromobenzylamine isomers was isolated for catalytic reduction with 3H2 at a commercial facility. Carrier N‐(2‐hydroxyethyl)‐N‐ethyl‐2‐methylbenzylamine was added to the crude tritiated product prior to refluxing in the presence of excess thionyl chloride. (3H)‐Xylamine was obtained as the hydrochloride salt and repeated recrystallizations yielded a radiochemically pure product with a specific activity of 3.09 Ci/mmol. Several analytical procedures established that the radiolabel was associated with xylamine.
Synthesis of trideuterated stanozolol labelled selectively at the 17‐methyl group
Authors: Johnston D. , Henderson K. 
Published: October 2006

AbstractA synthetic procedure for stanozolol‐d3is described. Deuterium labelling was achieved by the Grignard reaction of androstan‐3β ‐ ol ‐ 17 ‐ one with deuterium labelled methyl magnesium iodide (CD3Mg I). The synthesis was achieved in five steps from Δ5‐androstan‐3‐β‐ol‐17‐one in an overall yield of 15%. The procedure resulted in a product which was selectively deuterated and chemically pure.
Tritium labelling of antidepressants with regard to their chemical structure
Authors: Buchman Ouri , Azran Jacques , Shimoni Michael 
Published: October 2006

AbstractDifferent methods of tritium incorporation have been applied to 14 available tricyclic antidepressant drugs. The specific activities of the labelled compounds are compared. The results are discussed by comparison with hydrogendeuterium exchange and with regard to the chemical structure of these derivatives.
The synthesis of 1‐[(1‐methylethyl) amino]‐3‐{[(4‐methyl‐thio)‐1‐naphthalenyl]OXY}‐2‐propanol hydrochloride‐naphthalene‐1114C: 4′‐methylthiopropranolol
Authors: Gransden D. F. , Roth G. A. , Takahashi I. T. 
Published: October 2006

AbstractThe antihypertensive drug, 1‐[(1‐methylethyl)amino]‐3‐{[(4‐methylthio)‐1‐naphthalenyl ]oxy} ‐2‐propanol hydrochloride has been labeled with carbon‐14 in the 1‐position of the naphthalene. A total of 18.76 mCi was prepared in five steps starting with 1‐naphthol‐1‐14C. The overall yield for the synthesis was 33.6% following five recrystallizations of the free base. The radiochemical purity of the hydrochloride product was 98.0% by high pressure liquid chromatography (HPLC)/liquid scintillation counting (LSC). The specific activity of the product was found to be 11.68 ∓ 0.45 mCi/mmole. Structural confirmation was done by infrared spectroscopy.
Regioselective deuteration kinetics of 2,3,6‐trimethyl‐4‐phenylpyrylium and 2,6‐dimethyl‐3,4‐diphenylpyrylium salts (1)
Authors: Balaban Alexandru T. , Balaban Teodor Silviu , Uncuta Cornelia , Gheorghiu Mircea D. , Chiraleu Filip 
Published: October 2006

AbstractThe deuteration of 2,3,6‐trimethyl‐4‐phenylpyrylium salts in D2O + D3CCN indicates that the 2‐methyl group is deuterated 3.3 times faster than the 6‐methyl group. The 1H‐NMR assignment is based on an unambiguous synthesis of the 2‐CD3‐congener; similar assignments were made for 2,3,6‐trimethyl‐4‐phenylpyridine, and lanthanide‐induced shifts were determined. The deuteration of 2,6‐dimethyl‐3,4‐diphenylpyrylium perchlorate in anhydrous HCOOD + NaOOCH (the assignment in 1H‐NMR spectra is straightforward owing to the shielding of 2‐methyl protons by the neighbouring orthogonal phenyl group) indicates similarly that the 2‐methyl group is deuterated 3.0 times faster than the 6‐methyl group. Though the relative rates for 2‐ and 6‐methyl groups do not differ sufficiently for preparative regioselective deuterations, the present findings raise interesting problems for M.O. calculations.
Derivatives of β‐adrenergic antagonists. Preparation of propranolol‐3,3‐2H2 and propranolol‐18O
Authors: Nelson Wendel L. , Bartels Michael J. 
Published: October 2006

AbstractSyntheses of 1‐(isopropylamino)‐3‐(1‐naphthoxy)‐2‐propanol‐3,3‐2H2 (propranolol‐3,3‐2H2) (1) and of 1‐(isopropylamino)‐3‐(1‐naphthoxy‐180)‐2‐propanol (propranolol‐180) (2) are described. Reaction of 1‐naphthol (3) with glycerol‐2,3‐acetonide‐1,1‐2H2 tosylate (4) afforded, after hydrolysis, 3‐(1‐naphthoxy)propane‐1,2‐diol‐3,3‐2H2 (5). Tosylation afforded the primary tosylate (6) which was converted into 3‐(1‐naphthoxy)‐1,2‐epoxypropane‐3,3‐2H2 (7). Reaction of 7 with isopropylamine afforded 1 in 31% overall yield from 4. Reaction of 1‐naphthol‐180 (8) with epichlorohydrin (pyridine) afforded a mixture of 1‐chloro‐3‐(1‐naphthoxy‐180)‐2‐propanol (9) and 1,2‐epoxy‐3‐(1‐naphthoxy‐180)propane (10), which was converted to chlorohydrin 9 with HCl. Reaction of 9 with isopropylamine afforded 2 in 60% overall yield from 1‐naphthol‐180.
[N‐methyl‐11C]‐scopolamine: Synthesis and distribution in rat brain
Authors: Vora Manhar M. , Finn Ronald D. , Boothe Thomas E. , Liskwosky David R. , Potter Lincoln T. 
Published: October 2006

AbstractThe muscarinic antagonist [N‐methyl‐11C]‐scopolamine was synthesized by reductive methylation of norscopolamine with H11CHO and sodium cyanoborohydride, and then purified using preparative high performance liquid chromatography (HPLC). Preliminary in vivo studies in rat suggest the distribution of this compound to parallel with the muscarine receptor population in the brain.
Synthese de L'Acide [Pyridinyl‐2‐(14C‐2,6) Dithio]‐3 Propanoique Reactif de Couplage Covalent
Authors: Noel J. P. , Pichat L. 
Published: October 2006

Abstract3‐([2,6‐14C]2‐pyridinyldithio) propanoic acid, a disulphide covalent coupling reagent was synthesized in 12 steps from sodium [14C] cyanide. Condensation of sodium [14C] cyanide with 1,3‐dibromopropane gave, after hydrolysis [1,5‐14C] glutaric acid: 4 which was converted into [1,5‐14C] glutarimide : 5 by heating at 280°C with anhydrous ammonia. The imide : 5 was then converted into [2, 6‐14C] 2, 6‐dichloropyridine: by 6 by treatment with phosphorous penta and trichlorides. Chlorine removal from 6 by hydrogen (Roney Nickel) gave [2, 6‐14C] pyridine: 7 which was isolated as the hydrochloride. The latter was tranformed into [2, 6‐14C] pyridine‐N‐oxide :11 by hydrogen peroxide treatment. 11 treated by acetic anhydride (15 hours ‐ 130°C) rearranged into 2‐acetyloxy [2, 6‐14C] pyridine: 12 which was hydrolysed into [2, 6‐14C] 2‐pyridone: 13. Thiation of the latter by P2S5 in xylene gave 2‐mercapto [2, 6‐14C] pyridine: 10 which was then oxidized into [2, 6‐14C] 2‐dipyridinyldisuplphide: 14 the chlorination of which lead to [2, 6‐14C] 2‐pyridinylsulfenyl chloride: 15 which was not isolated. It was condensed with 3‐mercapto propanoic acid to give 1 with an overall yield of 4% based on sodium cyanide ‐ Specific activity was 55 mCi/mMol. The radiochemical purity checked by TLC and HPLC was 98.7%.
Deuteration with Lindlar's catalyst: Effects of various poisons on isotopic purity
Authors: Adlof R. O. , Emken E. A. 
Published: October 2006

AbstractThe Lindlar‐catalysed deuteration of methyl stearolate was studied to determine the effect of various poisons on the rate of reaction and on the isotopic purity of the methyl oleate‐9, 10‐d2 produced. Poisons containing both exchangable and nonexchangable α protons on the heterocyclic ring [quinoline, quinaldine, γ‐collidine, acridine, and pyridine] were used. All poisons yielded methyl oleate‐9, 10‐d2 having 94–97% isotopic purity. Very little over‐reduction of oleate to stearate occurred. Lindlar‐catalysed H‐D exchange involving the poisons was not significant.
Deuterated anabolic drugs. Part 2 synthesis of (R,S)‐3, 4‐bis(4‐hydroxyphenyl)‐[2,2,5,5‐d 4]hexane (HEX‐d4) and (E,E)‐3,4‐bis(4‐hydroxyphenyl)‐[2,5‐d2]hexa‐2,4‐diene (DE‐d2)
Authors: Zomer Gijsbert , Derks Henk J. G. M. , Wynberg Hans 
Published: October 2006

AbstractHexestrol‐d4 was synthesized from 1‐hydroxy‐1p‐methoxyphenyl‐[2,2‐d2]propane (7) by reductive coupling. The preparation of 7 involved reduction of p‐methoxy‐[2,2‐d2]propiophenone (2b) obtained by exchange deuteration. Dienestrol‐d2 was synthesized from p‐hydroxy‐[2,2‐d2]propiophenone by pinacol coupling followed by dehydratation of the coupling product using acetic anhydride/acetyl chloride.
Deuteration of verapamil by acid catalyzed exchange
Authors: Nelson Wendel L. , Bartels Michael J. 
Published: October 2006

AbstractDeuteration of verapamil, 5‐[(3,4‐dimethoxyphenylethyl)methyl‐amino]‐2‐(3,4‐dimethoxyphenyl)‐2‐isopropyvaleronitrile, an important calcium channel antagonist was accomplished by direct exchange in 25% 2H2SO4 in 2H2O. Refluxing for 140 hr incorporated 4–6 atoms of deuterium, which were distributed into both aromatic rings, but primarily in the ring attached through position 5 of the valeronitrile moiety.
Deuterium labelling of the GABA agonist thiomuscimol
Authors: Jacobsen Poul , Krogsgaard‐Larsen Povl 
Published: October 2006

AbstractDeuterium labelled thiomuscimol (6) was synthesized via catalytic deuteration in strongly basic C2H3O2H‐2H2O (9:1) of 3‐methoxy‐4‐bromo‐5‐(N‐methoxycarbony Iaminomethyl)isothiazole (3). The replacement of bromine by deuterium was accompanied by partial exchange of the side chain methylene protons for deuterium and by complete reesterification of the methoxycarbonyl group. Acid catalyzed deprotection of the reduction product 3‐methoxy‐4‐[2H]‐5‐(N‐[2H]methoxycarbonylamino[2H]methyl)isothiazole (5) gave 6 with only minor loss of deuterium from the ring and side chain.