Efficient synthesis of (1R, 2S) and (1S, 2R)-2-aminocyclopentanecarboxylic acid ethyl ester derivatives in enantiomerically pure form

…, F Ruebsam, Z Sun, CV Tran, AX Xiang, Y Zhou

Index: Dragovich, Peter S.; Murphy, Douglas E.; Dao, Kimkim; Kim, Sun Hee; Li, Lian-Sheng; Ruebsam, Frank; Sun, Zhongxiang; Tran, Chinh V.; Xiang, Alan X.; Zhou, Yuefen Tetrahedron Asymmetry, 2008 , vol. 19, # 24 p. 2796 - 2803

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Citation Number: 6

Abstract

A 4-step synthesis of an optically active synthetic intermediate [(1R, 2S)-2-(4′- fluorobenzylamino) cyclopentanecarboxylic acid ethyl ester complex with (S)-(+)-mandelic acid; compound 12,> 99% de] required for the preparation of a promising HCV NS5B polymerase inhibitor is reported. This process utilizes mandelic acid as a resolving agent, which can be recovered in good yield by a simple extraction. An optimized version of the ...