An efficient synthesis of (1S, 2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir


Demir A. , Aksoy-Cam H., Camkerten N., Hamamci H. , Doganel F.

TURKISH JOURNAL OF CHEMISTRY, vol.24, no.2, pp.141-146, 2000 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 24 Issue: 2
  • Publication Date: 2000
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.141-146

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% cis selectivity.