Patent ID: 8791300

Claim:
A process for preparing a substituted dimethyl-(3-arylbutyl)amine compound corresponding to formula III: wherein R 1 , R 1′ , R 2 , R 3 each independently denote —H or —C 1-5 -alkyl, R 4 , R 4′ , R 5 , R 5′ , R 6 are identical or different and each represent —H, —OH, —C 1-4 -alkyl, —O—C 1-4 -alkyl, partly fluorinated or perfluorinated —C 1-4 -alkyl, partly fluorinated or perfluorinated —O—C 1-4 -alkyl, —O—CH 2 ) n -phenyl where n is 1, 2 or 3, F, Cl or OR 8 , or two adjacent radicals R 4 and R 5 , R 5 and R 6 , R 6 and R 5′ or R 5′ and R 4′ represent a group —OCH═CHO—, —CH═C(R 9 )—O—, —CH═C(R 9 )—S— or —CH═CH—C(OR 10 )═CH— as part of a ring, with the proviso that the other particular radicals R 6 , R 5 and R 4 ′, R 4 , R 5′ and R 6′ , R 4 , R 5 and R 4′ or R 4 , R 5 and R 6 have the abovementioned meaning, R 8 denotes —CO—C 1-5 -alkyl, —PO(O—C 1-4 -alkyl) 2 , —CO—C 6 H 4 —R 11 , —CO(O—C 1-5 -alkyl), —CO—CHR 12 —NHR 13 , —CO—NH—C 6 H 3 —(R 14 ) 2 or an unsubstituted or substituted pyridyl, thienyl, thiazolyl or phenyl group, R 9 denotes —H or —C 1-4 -alkyl, R 10 denotes —H or —C 1-3 -alkyl, R 11 denotes —OC(O)—C 1-3 -alkyl in the ortho-position or —CH 2 —N—(R 15 ) 2 in the meta- or para-position, wherein R 15 in each case denotes —C 1-4 -alkyl or the two radicals R 15 together with the bridging nitrogen atom form a 4-morpholino radical, R 12 and R 13 are identical or different and each represent —H, —C 1-6 -alkyl or —C 3-8 -cycloalkyl, or R 12 and R 13 together denote —(CH 2 ) 3-8 — as part of a ring, and R 14 denotes —H, —OH, —C 1-7 -alkyl, partly fluorinated or perfluorinated —C 1-7 -alkyl, —OC 1-7 -alkyl, -phenyl, —O-aryl, —F or —Cl, with the proviso that R 14 may be identical or different, said process comprising: (a) choosing a homogeneous catalyst comprising a soluble rhodium salt or rhodium complex including an appropriate chiral diphosphine ligand with two secondary phosphine groups to prepare a specific diastereomer of a compound of formula III in a ratio of greater than or equal to 70:30 in favor of the specific diastereomer; and (b) reacting a substituted dimethyl-(3-arylbut-3-enyl)amine compound corresponding to formula II: or a salt thereof, wherein R 1 and R 3 are methyl, R 1′ and R 2 are H, R 4 , R 4′ , R 5′ , and R 6 are H, and R 5 is OCH 3 , in the presence of hydrogen and the homogeneous catalyst having the appropriate chiral diphosphine ligand, wherein the chiral diphosphine ligands is: to prepare the specific diastereomer of the compound of formula III in the ratio of greater than or equal to 70:30 in favor of the specific diastereomer.