Tetrahedron: Asymmetry

Resolution of racemic cis-1-amino-2-indanol by diastereomeric salt formation with (S)-2-phenylpropionic acid

R Sakurai, K Sakai

Index: Sakurai, Rumiko; Sakai, Kenichi Tetrahedron Asymmetry, 2003 , vol. 14, # 4 p. 411 - 413

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Citation Number: 15

Abstract

Resolution of racemic cis-1-amino-2-indanol 1, a key intermediate for the synthesis of indinavir, is reported. The conditions were optimized for an industrial-scale resolution of racemic cis-1 using (S)-2-phenylpropionic acid 6 as the resolving agent and ethanol as the solvent. The less-soluble diastereomeric salt,(1R, 2S)-1·(S)-6, was obtained in 35% yield with 99% de (E> 69%) by crystallization. Resolving agent 6 was efficiently recovered from ...