182575-38-8Relevant articles and documents
A practical synthesis of (1S, 2R)-1-amino-2-indanol, a key component of HIV protease inhibitor, indinavir
Kajiro, Hiroshi,Mitamura, Shu-Ichi,Mori, Atsunori,Hiyama, Tamejiro
, p. 51 - 52 (1998)
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.
A practical synthesis of (1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor, indinavir
Kajiro, Hiroshi,Mitamura, Shuichi,Mori, Atsunori,Hiyama, Tamejiro
, p. 1093 - 1100 (2007/10/03)
A synthesis of (1S,2R)-1-amino-2-indanol (1), a key component of an HIV protease inhibitor, was accomplished through (R)-2-hydroxy-1-indanone ((R)- 3), which was prepared by an intramolecular Friedel-Crafts acylation of (R)2- acetoxy-3-phenylpropanoic acid readily available from D-(R)-phenylalanine. Alternatively, (R)-3 was obtained by an enzymatic resolution of (±)-2- acetoxy-1-indanone. Ketone (R)-3 was convened into 1 through an oxime formation and diastereoselective hydrogenation.
