An Efficient Synthesis of (1 S , 2 R )-1-Amino-2-Indanol, A Key Intermediate of HIV Protease Inhibitor, Indinavir

Authors: AYHAN S. DEMİR, HİLAL AKSOY-CAM, NURETTİN CAMKETEN, HALUK HAMAMCI, FATOŞ DOĞANEL

Abstract: (1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor is synthesized in four steps starting from indanone. The Mn(OAC)_3 mediated acetoxylation of indanone followed by fungus catalyzed hydrolysis of acetoxyindanone furnished optically pure \alpha-hydroxy indanone. Formation and enantioselective reduction of oxime ether of 2-hydroxyindanone afforded (1S, 2R)-1-amino-2-indanol in 97% {\it cis} selectivity.

Keywords: Manganese(III) oxidation, imine reduction, enantioselective hydrolysis, 1-amino-2-indanol

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