New chemical and chemo-enzymatic routes for the synthesis of (RS)-and (S)-enciprazine

L Banoth, TK Narayan, UC Banerjee

Index: Banoth, Linga; Narayan, Thete Karuna; Banerjee, Uttam C. Tetrahedron Asymmetry, 2012 , vol. 23, # 17 p. 1272 - 1278

Full Text: HTML

Citation Number: 9

Abstract

The chemo-enzymatic synthesis of racemic and enantiopure (RS)-and (S)-enciprazine 1, a non-benzodiazepine anxiolytic drug, is described herein. The synthesis started from 1-(2- methoxyphenyl) piperazine 3, which was treated with 2-(chloromethyl) oxirane (RS)-4 using lithium bromide to afford a racemic alcohol, 1-chloro-3-(4-(2-methoxyphenyl) piperazin-1-yl) propan-2-ol (RS)-6 in 85% yield. Intermediate (S)-6 was synthesized from racemic alcohol ...