Process for the enantioselective synthesis of 2(R)-benzylsuccinic acid monoamide derivatives

US5321139A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Ulrich Lerch
• Heiner Jendralla · Frankfurt, DE
• Bernhard Seuring · Frankfurt am Main, DE
• Rainer Henning · Tokyo, JP

Key dates

• Filing date: Feb 16, 1993
• Grant date: Jun 14, 1994
• Expiry date: Feb 16, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F15/008
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Two processes are described for the preparation of the optically pure compounds of formula 1: ##STR1## in which R.sup.1 and R.sup.2 are e.g. alkyl, R.sup.3 and R.sup.4 are e.g. hydrogen and R.sup.5 is e.g. hydrogen. Both processes include, as key steps, the enantioselective hydrogenation of a C.dbd.C double bond and the regioselective formation of a dicarboxylic acid monoamide derivative. In one process a phenylitaconic acid derivative is asymmetrically hydrogenated to give an optically active (R)-benzylsuccinic acid which is then converted to a diester, said diester being converted to the monoamide compound of formula 1. In the second process, a phenylitaconic acid derivative is converted to its anhydride, and the anhydride is then converted to a monoamide which is then asymmetrically hydrogenated to give the compound of formula 1.