bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthèse de l'Oxetorone (14C‐6) : (diméthylamino‐3 propylidène‐1)‐6 benzofuro [2,3‐e] 12H‐benzo [b] oxépine (14C‐6). Séparation chromatographique des isomères (E) et (Z)
Authors: Noel J. P. , Pichat L. , Benakis A. 
Published: October 2006

AbstractSynthesis and chromatographic separation of (E) and (Z) isomers of [6‐14C] oxetorone : [6‐14C] 6‐(3‐Dimethylaminopropylidene)[2, 3‐e] benzofuro‐12H‐benzo [b] oxepin*, hydrogen fumarate. A new synthesis of [6‐14C] oxetorone was devised allowing the three step preparation from 14CO2 of this drug used in the treatment of migraine. 2‐bromo‐3‐phenoxymethyl benzo [b] furan : 10 was prepared from 3‐methyl [b] furan 7. In diethyl ether 10 gave with n‐butyllithium the corresponding : 2‐lithio 3‐phenoxymethyl benzo [b] furan the carbonation of which with 14CO2 gave [2‐carboxy 14C] 3‐phenoxymethyl benzo [b] furan in a 70% yield based on 14CO2. The carboxylic acid 5 was transformed into the corresponding acyl halide which was ring closed into [6‐14C] oxepinone 6. Condensation of the latter with 3‐dimethylaminopropyl magnesium chloride followed by dehydration under hydrochloric acid treatment and isolation as fumarate gave [6‐14C] oxetorone with an overall yield of 24% based on 14CO2. The (E) and (Z) isomers of oxetorone were separated by reverse phase HPLC.
A total synthesis of [9′, 10′‐3H]‐labelled paf‐acether
Authors: Wichrowski Boguslaw , Michel Elie , Heymans Françoise , Roy Jean , Morgat Jean‐Louis , Godfroid Jean‐Jacques 
Published: October 2006

Abstract1‐O‐octadecen‐[9′, 10′]‐yl 2‐o‐benzyl sn‐glycero‐3‐phosrylcholine was obtained from 1‐O‐octadecen‐[9′, 10′]‐yl sn‐glycerol by tritylation, benzylation and phosphorylation with 2‐bromoethyl phosphoryl dichloride followed with trimethylamine reaction. Catalytic tritiation of the double bond led to labelled “lyso” PAF‐acether from which PAF‐acether with a specific radioactivity between 40 and 50 Ci/mmole was obtained by acetylation.
A new approach to the synthesis of 14C labelled DL‐malic acid
Authors: Ramamurthy T. V. , Viswanathan K. V. 
Published: October 2006

AbstractThe 2‐carbon units, glycine and glyoxylate are combined by a mild reaction via the copper chelate of glycine. The resulting β‐hydroxy aspartic acid is converted to DL‐malic acid by means of hydroxylamine 0‐sulfonic acid. The overall yields are in the range of 35–50% in submillimolar preparations.
The synthesis of [14C]‐L‐lysyl‐N‐(2‐benzoyl‐4‐chlorophenyl)‐N‐methyl glycinamide
Authors: Harrison J. M. 
Published: October 2006

AbstractA procedure has been developed for the synthesis of L‐lysyl‐N‐(2‐benzoyl‐4‐chlorophenyl)‐N‐methyl glycinamide labelled with carbon‐14. The label was introduced using [14C]carbon dioxide to prepare the intermediate [carboxyl‐14C]benzoic acid.
Synthesis and biodistribution of radioiodinated‐5‐iodonicotine
Authors: Chan S. M. , Basmadjian G. P. , Marten D. F. , Sadek S. A. , Magarian R. A. , Grunder J. R. , Ice R. D. 
Published: October 2006

Abstract5‐Bromonicotine, synthesized from nicotinic acid, was autoclaved with Na125I in the presence of copper sulfate and glacial acetic acid to give 5‐[125I]iodonicotine. The radiochemical yield was 25.3%. The specific activity of the product was approximately 61 mCi/mmole. Biodistribution studies of 5‐[125I]iodonicotine, performed in rats, showed that the labelled compound accummulated rapidly in the brain and the adrenal gland. The highest uptake of radioactivity in these organs occurred at 5 minutes after administration. The brain‐to‐blood and the adrenal‐to‐blood ratios at this time interval were 2.6:1 and 3.3:1 respectively.
Silica gel‐assisted reduction of nitrostyrenes to 2‐aryl‐2‐[2H]‐1‐nitroethanes with sodium borodeuteride
Authors: Sinhababu Achintya K. , Borchardt Ronald T. 
Published: October 2006

AbstractReduction of nitrostyrenes with sodium borodeuteride in the presence of silica gel (70‐270 mesh) in a mixture of chloroform and 2‐propanol gave the corresponding deuterated nitroethanes in near quantitative yields, free of dimeric products with 72‐81% deuterium incorporation. The method was applied to the synthesis of 2‐phenyl‐, 2‐[4‐methoxyphenyl]‐, 2‐[3,4‐dimethoxyphenyl]‐, 2‐[3,4,5‐trimethoxyphenyl]‐, and 2‐[2,4,5‐trimethoxyphenyl]‐2‐[2H]‐l‐nitroethanes.
Self‐decomposition of DL‐/methyl‐14C/carnitine to labelled β‐methylcholine and acetonyltrimethylammonium
Authors: Löster Heinz , Seim Hermann , Strack Erich 
Published: October 2006

AbstractThe self‐decomposition rate of DL‐/methyl‐14C/carnitine (32 mCi/mmol) in the crystalline betaine form was studied. It was found to be decomposed to 39.5 % in 4.5 years. On this basis a self‐decomposition coefficient G = 4.2 was calculated for the solid state. DL‐/N‐methyl‐14C/β‐methylcholine was the most important labelled product of decomposition (12%). /N‐methyl‐14C/acetonyl‐trimethylammonium was also present among the radiolytic products (2%). It was detected as its 2,4‐dinitrophenylhydrazone by means of thin‐layer chromatographic separation and autoradiography.
Preparation of 2,2,2(2H3)‐diazoethane
Authors: Meese Claus O. 
Published: October 2006

Abstract2,2,2(2H3) Ethyl‐N‐nitroso‐p‐toluenesulfonamide 6a, prepared in three steps from trideuteroacetonitrile 2a (overall yield 71%), has been subjected to alkaline decomposition to give after co‐distillation with ether/n‐hexane solutions of 2,2,2(2H3)‐diazoethane 1a. As shown by quantitative studies and from NMR and mass spectra, respectively, carboxylic acids were completely converted by 1a under mild reaction conditions into highly labelled (>96% d3, (<0.3% d0) 2,2,2(2H3)‐ethyl esters. The ready preparation of 1(2H1,2)‐ethyl 4‐nitrobenzoate 15 from 9 and unlabelled 1b under H/D exchange conditions illustrates the possibility of further introduction of 2H or 3H into an ethyl group. The molar extinction coefficient of 1a, b has been determined (ϵ (470 nm)=8.4).
[103RU]‐markierte ruthenocen‐der ivate biogener amine
Authors: Wenzel M. , Asindraza P. , Schachschneider G. 
Published: October 2006

AbstractThe ruthenocene derivatives of different biogenic amines labelled with 103RU in the ruthenocene moity were synthesized. In a first step the central atom of ferrocene was exchanged with 103RuCl3 yielding [103RU]‐ruthenocene, by vilsmeier‐formylation the radioactive ruthenocene aldehyde was synthesized which was condensed with the desired amine to the Schiff'sche base, followed by the reduction of the CN double bond by NaBH4.
The aryl group controls the α/γ regioselectivity in deuterations of 2‐(p‐substituted benzyl)‐4,6‐dimethylpyrylium salts (1)
Authors: Balaban Alexandru T. , Gheorghiu Mircea D. , Balaban Teodor Silviu 
Published: October 2006

AbstractA kinetic study is reported for the deuteration (in sodium formate‐con‐taning HCOOD at 50–73°) of 2‐benzyl‐4,6‐dimethylpyrylium perchlorate and of its derivatives possessing para‐substituents at the phenyl ring (NO2, Cl, Me, OMe). Intramolecular comparison of deuteration rates indicates that the 4‐methyl is always deuterated 8–10 times faster than the 6‐methyl; however, the 2‐methylene group is deuterated with a rate dictated by the nature of the aryl group : faster than the 4‐methyl with p‐NO2 and p‐C1 substituents, more slowly than the γ‐methyl group with p‐Me and p‐OMe substituents. Hammett plots show good correlations for relative deuteration rates of the methylene group, and for 1H‐NMR chemical shifts for methyl and methylene protons.
The preparation of carbon‐14 labelled 1‐[4‐(2‐diethylamino‐ethoxy) phenyl]‐1, 2‐diphenyl‐2‐chloroethene (clomiphene) and 1‐[4‐(2‐(N‐pyrrolidinyl) ethoxy) phenyl]‐2‐(4‐methoxyphenyl)‐2‐nitro‐2‐phenylethene (CI‐628, nitromiphene)
Authors: Ruenitz Peter C. , Bagley Jerome R. 
Published: October 2006

AbstractThe preparation of [14C] clomiphene and [14C] nitromiphene from [methylene‐14C] benzyl chloride is described. The overall radio‐chemical yield and specific activity of the former are 53% and 0.53 mCi/mmol and those of the latter are 26% and 0.23 mCi/mmol. The method described is of micromolar scale designed for maintaining cost economy while yielding final products of sufficient radioactivity for in vitro and in vivo metabolism studies.
13C labeled benzo[a]pyrenes and derivatives 3. Benzo[a]pyrene‐4,5‐oxide‐4‐13C and benzo[a]pyrene‐4,5‐oxide‐5‐13C
Authors: Hylarides Mark D. , Daub Guido H. , Vanderjagt David L. , Silverman I. Robert 
Published: October 2006

AbstractThe synthesis of benzo[a]pyrene‐4,5‐oxide‐4‐13C and benzo[a]‐pyrene‐4,5‐oxide‐5‐13C from the corresponding 13C labeled 4,5‐dihydrobenzo[a]‐pyrene‐4,5‐diones is described. Reduction of the quinone with potassium borohydride in freshly distilled peroxide‐free 2‐propanol gave the trans‐diol which was directly cyclized to the oxide by refluxing with DMF‐DMA in chloroform/OMF. The overall yield of the oxide was 48–53% for the two steps. The requisite quinones were available in five steps from 1,2‐dihydrochrysen‐4(3H)‐one as described in an earlier paper. Overall yield of the oxide from the chrysenone was 27%. 13C NMR of the labeled oxides in CDCl3 gave chemical shifts of 56.80 for C5 and 56.20 for C4 (δC from TMS) of benzo[a]pyrene‐4,5‐oxide.
Tritium labelling of benzamide drugs
Authors: Pri‐Bar Ilan , Buchman Ouri 
Published: October 2006

AbstractMethods for tritiation of sulpiride, sultopride and metoclopramide were developed and optimized. 3H‐sulpiride (7.1 Ci/mmol), 3H‐sultopride (2.1 Ci/mmol) and 3H‐metoclopramide (18.0 Ci/mmol) were obtained by hydrodebromination of the related bromo derivatives. The bromo derivatives were prepared, in turn, by appropriate procedures specified for each case.
Synthesis of C19 steroid monosulphates labelled with deuterium at specific positions
Authors: Rudqvist Ulf 
Published: October 2006

AbstractSynthesis of C19 steroid monosulphates labelled with deuterium is reported. Deuterium was introduced either at hydroxylated carbons or in methylene groups, in order to permit use of the steroids in studies of intermolecular hydrogen transfer in vivo. Methylene groups were deuterated by equilibration of carbonyl α‐hydrogens with deuterium oxide. Deuterium at hydroxylated carbons was introduced by metal deuteride reduction. The sulphate group was introduced in the final step of a reaction sequence or, in some cases, in the step preceding the final one followed by removal of an acetate group.
Synthesis of [α‐14C]‐benzylguanidine
Authors: Inbasekaran Muthiah N. , Mangner Thomas J. , Wieland Donald M. 
Published: October 2006

Abstract[α‐14C]‐benzylguanidine (1) having a specific activity of 14 mCi/mmol was synthesized in 55% yield (isolated) by reacting [α‐14C]‐benzylamine hydrochloride and cyanamide in 1‐butanol.
Preparation of specifically‐labelled buspirone ‐14C and buspirone ‐ 15N2
Authors: Covington R. R. , New J. S. , Yevich J. P. , Temple D. L. 
Published: October 2006

AbstractBuspirone 1 is a novel, clinically effective anxiolytic agent which is devoid of the sedative, anticonvulsant or muscle relaxant properties normally associated with the benzodiazepines. Buspirone labelled with both radioactive (14C) and stable (15N) isotopes was required in order to investigate the metabolism of the compound. The synthesis of both labelled compounds beginning with either urea ‐ 14C or urea ‐ 15N2 is described.
Synthesis of hexadeuterated diethylstilbestrol ([1,1,1,6,6,6‐d6]‐E‐3,4‐di‐(4‐hydroxyphenyl)‐hex‐3‐ene)
Authors: Zomer Gijsbert , Derks Henk J. G. M. , Wynberg Hans 
Published: October 2006

Abstract[1,1,1,6,6,6‐d6]‐E‐3,4‐di‐(4‐hydroxyphenyl)‐hex‐3‐ene was synthesized from [1,1,1‐d3]‐4‐methoxypropiophenone by reductive coupling. The preparation of [1,1,1‐d3]‐4‐methoxypropiophenone involved reaction of p‐anisoylchloride with perdeuterated diethyl‐cadmium followed by back‐exchange of the alpha protons.
The preparation of [15N]‐ and [1‐13C]‐2‐naphthylamine and their conversions into [15N, 15N′]‐ and [1,1′‐13C2]‐2,2′‐azonaphthalene
Authors: Gruszecka Ewa , Shine Henry J. 
Published: October 2006

AbstractSpecifically labelled [15N]‐2‐naphthylamine and [1‐13C]‐2‐naphthylamine have been synthesized with approx. 99% label abundance. The correspondingly highly‐enriched, doubly‐labelled 2,2′‐azonaphthalenes have been made.
Synthesis of 14C labelled metalaxyl and furalaxyl
Authors: Westcott Neil D. , Reichle Randy A. 
Published: October 2006

AbstractThe syntheses of the 14C labelled fungicides, metalaxyl and furalaxyl, are described. Sodium 2‐[14C]‐propionate was brominated at C‐2 and esterified with diazomethane to produce methyl 2‐bromo‐propionate. This bromopropionate was reacted with 2,6‐dimethyl‐aniline to produce methyl N‐(2,6‐xylyl)‐DL‐alaninate which was acylated with either methoxyacetyl chloride or 2‐furoyl chloride to produce 14C labelled metalaxyl and furalaxyl respectively.
Synthesis of tritiated cromolyn diethyl ester
Authors: Wyrick Steven D. , Ranga V. 
Published: October 2006

AbstractWe report here the synthesis of tritiated cromolyn diethyl ester of high specific activity and acceptable stability for use in in vitro and in vivo models of experimental asthma in the guinea pig. Preparation of an aryl brominated precursor, 1,3‐bis‐(2‐acetyl‐3‐hydroxy −6‐bromophenoxy)‐2‐propanol, followed by catalytic debromination with tritium gas and two subsequent synthetic steps atforded tritiated cromolyn diethyl ester with a specific activity of 135 mCi/mg (71 Ci/mmol).
Regioselective deuterium labelling of aromatic acids, amides and amines using group VIII metal catalysts
Authors: Lockley W J S 
Published: October 2006

AbstractOrtho‐deuterated arylcarboxylic acids and their sodium salts may be prepared with high regioselectivity by isotopic exchange with deuterium oxide in the presence of a range of commercially available group VIII metal complexes. When rhodium trichloride trihydrate is employed a range of arylcarboxamides and arylmethanamines are also selectively labelled at the ortho‐positions.
Labeled bile acids II: Methyl 3β‐hydroxychol‐5‐en‐24‐oate, labeled with 13C and/or 2H
Authors: Byon Chang Yon , Gut Marcel , Lai Chee Kong 
Published: October 2006

AbstractThe incorporation of 13C, and/or 2H2, into methyl 3β‐hydroxychol‐5‐en‐24‐oate to give products with an abundance of the isotopic label at a specific position, useful for metabolism studies, has been accomplished.
Synthesis of 14C‐labelled methylazoxymethanol acetate of high specific activity
Authors: Cazer Frederick D. , Barnela Satish B. , Kumar Kultar S. , Kamat Prabhakar L. , Milo George E. , Witiak Donald T. 
Published: October 2006

AbstractThe micro‐scale synthesis of 14C‐labelled methylazoxymethanol acetate (14C‐MAM‐acetate) having a specific activity of 110 mCi/mmol was accomplished in 25% yield from N,N′‐[methyl‐14C] ‐dimethylhydrazine with a specific activity of 112.5mCi/mmol.
Tritium labeling of potential lipophilic myelin probes
Authors: Ehrenkaufer R. L. E. , Agranoff B. W. , Bieszki J. , Frey K. , Hays S. , Jewett D. 
Published: October 2006

AbstractTwo potential lipophilic myelin imaging agents (1,1,2,2‐tetrafluoro‐1,2‐diphenylethane and 1‐fluoroadamantane) were tritium labeled. The most effective method employed the microwave discharge activation of tritium gas technique and resulted in specific activities of 177 mCi/mmol for 1,1,2,2‐tetrafluoro‐1,2‐diphenylethane and 593 mCi/mmol for 1‐fluoroadamantane. Using this tritiation method significant amounts of tritium‐for‐fluorine substitution was also observed in the labeling of 1‐fluoroadamatane, resulting in nearly equivalent amounts of tritiated adamantane and fluoroadamantane.
Synthesis of (S)‐Nτ‐[D3] methylhistidine
Authors: Yuan Sun‐Shine , Ajami Alfred M. 
Published: October 2006

Abstract(S)‐Histidine methyl ester was converted on a 20 g scale to its Nα, Nπ‐cyclic urea by treatment with carbonyl diimidazole. The Nτ position was alkylated with [D3]‐methyl iodide and the product was hydrolyzed to give isomerically and isotopically pure Nτ‐[D3] methylhistidine, without significant loss of optical activity.
Stereospecific synthesis of adenosine cyclic 3′,5′‐RP‐ and SP‐phosphoro‐[35S]thioates
Authors: Baraniak Janina , Reimschüssel Wtadystaw , Rudziński Juliusz , Stec Wojciech J. 
Published: October 2006

AbstractStereospecific reaction of both diastereoisomers of O2′,N6,N6‐tribenzoyladenosine cyclic 3′,5′‐phosphoranilidates (1) with sodium hydride and carbon [35S]disulphide gave, after removal of the protective groups, the desired RP — and SP‐diastereoisomers of [35S]cAMPS (2).
Methodes de Synthese de l'Acide Agarique Racemique Marque au 14C (acide α‐cetyl citrique (carboxyle‐1 14C) OU acide hydroxy‐2 nonadecanetricarboxylique‐1,2 (carboxyle 14CO)‐3)
Authors: Lellouche J. P. , Beaucourt J. P. , Pichat L. 
Published: October 2006

AbstractRacemic [3‐carboxyl 14C] agaric acid triethyl ester was prepared in low yield by treatment of ethyl 2‐ethoxalyl octadecanoate 2 with either ethyl lithioacetate or ethyl bromoacetate, zinc and methyl borate. In another approach, lithio ethynyltrimethylsilane 6 was condensed with 2 to give 7 which, with dicyclohexylborane 8, gave the vinyl borane 9; the latter, by hydrogen peroxide oxidation followed by reaction of diazomethane gave the mixed ester 11 in low yield. [3‐carboxyl 14C] Agaric acid, specific activity 57 mCi/mmol, was obtained from 5 or 11 by saponification with lithium hydroxide in 1,2‐dimethoxyethane. The best overall yield from ethyl [1‐14C] stearate was 18%.
Synthesis of 14C‐labeled aminoglutethimide
Authors: Chaudhuri Naba K. , Servando Ofelia , Sung Ming‐Sang , Baumann Heinz 
Published: October 2006

AbstractA new procedure has been developed for the synthesis of 14C‐labeled glutethimide with an improved yield from K14CN. In this procedure benzyl cyanide prepared from benzyl chloride and K14CN was almost quantitatively monoethylated by an ion‐pair extraction method using 50% excess of tetrabutylammonium hydroxide as the catalyst. Michael addition of methyl acrylate to monoethylbenzyl cyanide followed by hydrolysis with H2SO4 gave glutethimide which was then nitrated (HNO3 + H2SO4) and catalytically reduced to aminoglutethimide. The best result was obtained when the intermediate para‐nitroglutethimide was isolated in pure form by crystallization and then reduced in the presence of 10% Pd/C. When the nitration product (which was a mixture of isomers) was reduced without purification, isolation of pure p‐aminoglutethimide was more difficult and the yield was much lower.
Carbon‐14 and tritium labeled guanadrel sulfate
Authors: Hsi Richard S. P. , Johnson Tommy D. , Stolle Wayne T. 
Published: October 2006

AbstractCarbon‐14 and tritium labeled (1,4‐dioxaspiro[4.5]dec‐2‐ylmethyl)guanidine sulfate, or guanadrel sulfateGuanadrel sulfate is the USAN name for (1,4‐dioxaspiro[4.5]dec‐2‐ylmethyl) guanidine sulfate.
(1) were synthesized. The carbon‐14 label was incorporated into the dioxolane ring portion of guanadrel sulfate. The tritium labels were introduced into the cyclohexane ring portion of the molecule, at the beta and gamma positions with respect to the ketal linkage. The ketal resulting from the reaction of the original 2‐cyclohexen‐1‐one with 3‐phthalimido‐1,2‐propanedial contained a double bond in the β‐γ position rather than the α‐β postion of the original 2‐cyclohexen‐1‐one. This double bond shift provided a convenient method of introducing tritium into the 3‐and 4‐positions of cyclohexanone. Proof of the double bond position is discussed.
Synthesis of 4‐hydroxy[phenyl‐U‐14C]coumarin
Authors: Nadian Allan K. 
Published: October 2006

AbstractRadiolabeled 4‐hydroxycoumarin was synthesized on a microscale by condensing [U‐14C]phenol and malonic acid in the presence of anhydrous zinc chloride and phosphorus oxychloride. The yield was 14% on a 0.5 mmol scale at a specific activity of 107 μCi/mmol.
Preparation of [18O]‐chlorocarbonylsulfenyl chloride
Authors: Mott Andrew W. , Eastep Steven J. , Słomczynska Urszula , Barany George 
Published: October 2006

Abstract[18O]‐Chlorocarbonylsulfenyl chloride with an isotopic purity of 92% was prepared in three steps starting with the [18O]‐hydrolysis of 2‐ethyl‐1,3‐dioxolane to [18O]‐propanal, which was then converted to [18O]‐O‐1‐methylpropyl S‐methyl dithiocarbonate, which was then chlorinated to give the title compound. Distilled yields for the three steps were 57%, 49%, and 40% respectively.
Synthesis of dl‐glutamine‐2,5‐15N2
Authors: Lagna William M. , Callery Patrick S. 
Published: October 2006

AbstractA two step synthesis of dl‐glutamine‐2,5‐15N2 is described. 2‐Oxapentanedioic acid was reacted with hydrazine sulfate‐15N2 to yield 6‐carboxy‐(2H)‐pyridazin‐3‐one‐1,2‐15N2, which was then reduced with hydrogen over 10% Pd/C catalyst to dl‐glutamine‐2,5‐15N2. Gas chromatography of the trimethylsilylated derivative of the labeled glutamine was used to establish purity. Mass spectra for dl‐glutamine‐15N2, dl‐glutamine and their intermediates, 6‐carboxy‐(2H)‐pyridazin‐3‐one‐1,2‐15N2 and 6‐carboxy‐(2H)‐pyridazin‐3‐one were consistent with assigned structures.
1‐cyano‐1‐(6‐phenoxy‐2‐pyridinyl‐2, 6‐14C)methyl 3‐(2,2‐dichloroethenyl)‐2, 2‐dimethyl‐cyclopropanecarboxylate
Authors: McKendry L. H. 
Published: October 2006

AbstractA 15.7 mCi sample of 99% radiochemically pure 1‐cyano‐1‐(6‐phenoxy‐2‐pyridinyl‐2,6‐14C)methyl 3‐(2,2‐dichloroethenyl)‐2,2‐dimethylcyclopropanecarboxylate with a specific activity of 21.3 mCi/mmole was prepared via a six step process from 2,6‐dichloropyridine‐2,6‐14C.
Synthesis of [carbonyl‐14C]‐ and (methoxy‐d3)‐labeled N‐[(2RS, 3RS)‐1‐benzyl‐2‐methyl‐3‐pyrrolidinyl] −5‐chloro‐2‐methoxy‐4‐(methylamino) benzamide (YM‐09151‐2). A new potent neuroleptic agent
Authors: Tamazawa Kazuharu , Arima Hideki 
Published: October 2006

AbstractA new potent neuroleptic agent YM‐09151‐2, N‐[(2RS, 3RS)‐1‐benzyl‐2‐methyl‐3‐pyrrolidinyl]‐5‐chloro‐2‐methoxy‐4‐ (methylamino) benzamide (10c), was labeled with carbon‐14 and deuterium for biochemical studies such as metabolism and 14 pharmacokinetics. The synthesis of [carbonyl‐14C]YM‐09151‐2 (10a) from 4‐amino‐2‐hydroxy‐[carboxyl‐14C] benzoic acid (1a) in six stages is described. Overall radiochemical yield was 79.1% at a specific activity of 21.18 mCi/mmol. (Methoxy‐d3)YM‐09151‐2 (10b) was prepared from methyl 2‐(methoxy‐d3)‐4‐(N‐methyl‐N‐tosylamido) benzoate (5b) which was obtained by the reaction of methyl 2‐hydroxy‐4‐(N‐methyl‐N‐tosylamido) benzoate (4c) with iodomethane‐d3. Overall yield of 10b was 60.8% from iodomethane‐d3.
Synthesis of 5‐hydroxy‐[6‐14C]‐methyl‐2‐di‐n‐propylaminotetralin
Authors: Koble Dale L. , Fischer Lawrence J. 
Published: October 2006

AbstractBy an improved synthesis, 5‐hydroxy‐6‐methyl‐2‐di‐n‐propylaminotetralin (DK‐118), a dopamine agonist, has been obtained in only six steps and in greater than 10% overall yield. This new synthesis has been used for the preparation of 5‐hydroxy‐[6‐14C]‐methyl‐2‐di‐n‐propylaminotetralin (I) to be used in metabolic studies. The 14C‐radiolabel was introduced near the end of the synthesis by an ortho‐specific formylation procedure using 14C‐paraformaldehyde.
Labeled bile acids V: Deuterium and carbon‐13 labeled cholic, chenodeoxycholic and ursodeoxycholic acids
Authors: Lai Chee Kong , Byon Chang Yon , Gut Marcel , Mostowicz Danuta , Anderson Warren G. 
Published: October 2006

AbstractThis paper describes a general, simple and short procedure for the introduction of stable isotopes (deuterium and carbon‐13) to the side chain of bile acids. The bisnorcholyl aldehydes of cholic and chenodeoxycholic acids are key intermediates, while the isotope is introduced by the Wittig condensation of [1,2‐13C2]‐(carbethoxymethylene)triphenyl‐phosphorane.
Syntheses of piperidine and granatanine doubly isotopically substituted with carbon‐13
Authors: Barna Jennifer J. C. , Robinson Michael J. T. 
Published: October 2006

AbstractSyntheses of (2,3‐13C2) piperidine and (1,2‐13C2) granatanine via (1,2‐13C2)‐glutaric acid have been achieved using a benzene ring as a potential carboxyl group.