Patent ID: 6858734

Claim:
A process for producing enantiomerically enriched derivative of (S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5 (4H)-acetic acid hydrocarbyl ester, represented by the formula: said process comprising the steps of: (a) contacting a derivative of N-2-chlorobenzaldehydeylidene-1-ethylamine-2 (2-thiophenyl)imine represented by the formula: and an HCN source, optionally in the presence of a catalyst represented by the formula: wherein said contacting is carried out at a temperature and length of time sufficient to form a derivative of enantiomerically enriched (S)-α,α-(2-thiophenylethylamino)(2-chlorophenyl)acetonitrile, represented by the formula: (b) contacting said derivative of enantiomerically enriched (S)-α,α-(2-thiophenylethylamino)(2-chlorophenyl)acetonitrile and a formaldehyde equivalent, optionally in the presence of a catalyst, wherein said contacting is carried out at a temperature and length of time sufficient to form a derivative of enantiomerically enriched α-5(4,5,6,7-tetrahydro[3,2-c]thienopyridyl)(2-chlorobenzyl)-nitrile, represented by the formula: and (c) contacting said derivative of enantiomerically enriched α-5(4,5,6,7-tetrahydro[3,2-c]thienopyridyl)(2-chlorobenzyl)-nitrile and a reagent capable of converting a cyano group into an ester group at a temperature and length of time sufficient to form a derivative of an enantiomerically enriched hydrocarbyl ester of (S)-α-(2-chlorophenyl)-6,7-dihydrothieno-[3,2-c]pyridine-5(4H)-acetic acid represented by the formula: wherein R 1 is a substituent at the 3, 4, 5 or 6 position of the chlorophenyl ring and R 2 is a substituent at the 4 or 5 position of the thiophene ring; wherein each R 1 and R 2 is independently selected from the group consisting of: H, linear, branched or cyclic alkyl of 1 to 22 carbon atoms, aryl of 6 to 22 carbon atoms, aralkyl of 7 to 22 carbon atoms, alkylaryl of 7 to 22 carbon atoms, halogen, cyano, nitro, amido, carbamato, imido, alkoxy, aryloxy, acyl, alkoxycarbonyl and trifluoromethyl; wherein R 3 is a hydrocarbyl group; and wherein R is selected from the group consisting of: phenyl, tolyl, xylyl, naphthyl, heteroaryl, amido, imido, carbamato, polystyrene beads, and a mixture thereof.