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

✍ Scribed by Rumiko Sakurai; Kenichi Sakai

Book ID: 104359649
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 89 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00022-3

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✦ Synopsis

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 the salt and the mother liquor.

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