Efficient oxidizing methods for the synthesis of oxandrolone intermediates

Chem Pharm Bull (Tokyo). 2004 Aug;52(8):989-91. doi: 10.1248/cpb.52.989.

Abstract

Mild, efficient and eco-friendly oxidation of 17alpha-methylandrostan-3beta-17beta-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65 degrees C, sodium hypochlorite and H2O2/Na2WO4 under phase transfer conditions to give 17beta-hydroxy-17alpha-methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H2O2/Na2WO4/PTC gave mestanolone in high yield and purity whereas sodium hypochlorite/PTC system yielded some chlorinated material along with the mestanolone. However, 1 with 2.5 equivalent of IBX gave 17beta-hydroxy-17alpha-methyl-Delta1-androsten-3-one (3) under the similar reaction conditions in good yield and single step reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstane-3,17-diol / chemistry*
  • Benzoic Acid / chemistry
  • Chlorine / chemistry
  • Dihydrotestosterone / analogs & derivatives*
  • Dihydrotestosterone / chemistry
  • Iodine / chemistry
  • Models, Chemical
  • Oxandrolone / chemical synthesis*
  • Oxidation-Reduction
  • Sodium Hypochlorite / chemistry

Substances

  • Dihydrotestosterone
  • Androstane-3,17-diol
  • Chlorine
  • Oxandrolone
  • Benzoic Acid
  • Iodine
  • Sodium Hypochlorite
  • mestanolone