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Synlett 1998; 1998(1): 51-52
DOI: 10.1055/s-1998-3126
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A Practical Synthesis of (1S,2R)-1-Amino-2-indanol, a Key Component of HIV Protease Inhibitor, Indinavir

Hiroshi Kajiro* , Shu-ichi Mitamura, Atsunori Mori, Tamejiro Hiyama
  • *Advanced Technology Research Laboratories, Nippon Steel Corporation, 3-35-1 Ida, Nakahara-ku, Kawasaki 211, Japan; Fax +81 (45) 9 24 52 24; E-mail: thiyamares.titech.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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The synthesis of (1S,2R)-1-amino-2-indanol, a key component of HIV protease inhibitor, is accomplished in eight steps from d-phenylalanine. The starting material is converted into 2-acetoxy-1-indanone in four steps involving intramolecular Friedel-Crafts cyclization. The stereochemically labile α-acetoxy ketone is hydrolyzed to 2-hydroxy-1-indanone using a catalytic amount of scandium triflate without any loss of the optical purity. Diastereoselective hydrogenation of α-hydroxy oxime, derived from the α-hydroxy ketone, gives the amino alcohol in 96% cis-selectivity. Optical purity of the starting material is perfectly retained throughout the transformations.

indinavir - 1-amino-2-indanol - hydroxyindanone scandium triflate - hydrogenation