A Novel Synthetic Method for Bepotastine, a Histamine H1 Receptor Antagonist

TH Ha, KH Suh, GS Lee

Index: Ha, Tae Hee; Suh, Kwee-Hyun; Lee, Gwan Sun Bulletin of the Korean Chemical Society, 2013 , vol. 34, # 2 p. 549 - 552

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Abstract

An efficient and alternative synthesis of enantiomerically pure (+)-(S)-4-(4-((4- chlorophenyl)(pyrid-2-yl) methoxy] piperidin-1-yl) butanoic acid, bepotastine (1) is described. The key resolution of (R/S)-bepotastine l-menthyl ester (3) is achived via diastereomeric salt crystallization using N-benzyloxycarbonyl-L-aspartic acid (NCbzLAA) as the resolving agent to provide (S)-bepotastine l-menthyl ester (S)-3. Hydrolysis of (S)- ...