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

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, (1 R ,2 S )- 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.