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■ Asymmetric Synthesis of the Enantiomers of 2-Aminomethyl-4-(4-fluorobenzyl)morpholine, an Intermediate of Mosapride, a Gastroprokinetic Agent

Toshiya Morie, Shiro Kato,* Hiroshi Harada, and Jun-ichi Matsumoto

*Discovery Research Laboratories, Dainippon Pharmaceutical Co., Ltd., Enoki 33-94, Suita, Osaka 564, Japan

Abstract

An efficient asymmetric synthesis of the enantiomers of 2-aminomethyl-4-(4-fluorobenzyl)morpholine (3) which has served as an intermediate of mosapride (1), a potential gastroprokinetic agent, was achieved by the conversion of enantiomeric 3-chloro-1-(4-fluorobenzylamino)-2-propanol (8) to the oxomorpholine (10) followed by reduction and amination, in approximately 35% overall yield with >98% ee. This synthetic route comprises the regioselective opening of homochiral epichlorohydrin (4) with 4-fluorobenzylamine, with retention of the configuration.