Efficient Oxidizing Methods for the Synthesis of Oxandrolone Intermediates

Sandeep K. Ginotra; Bhupender S. Chhikara; Manish Singh; Ramesh Chandra; Vibha Tandon

doi:10.1248/cpb.52.989

Notes

Efficient Oxidizing Methods for the Synthesis of Oxandrolone Intermediates

Sandeep K. Ginotra, Bhupender S. Chhikara, Manish Singh, Ramesh Chandra, Vibha Tandon

Author information

Keywords: steroid, oxidation, 2-iodoxy benzoic acid (IBX), NaOCl, hydrogenperoxide, dehydrogenation

JOURNAL FREE ACCESS

2004 Volume 52 Issue 8 Pages 989-991

DOI https://doi.org/10.1248/cpb.52.989

Details

Abstract

Mild, efficient and eco-friendly oxidation of 17α-methylandrostan-3β-17β-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65 °C, sodium hypochlorite and H₂O₂/Na₂WO₄ under phase transfer conditions to give 17β-hydroxy-17α-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 17β-hydroxy-17α-methyl-Δ¹-androsten-3-one (3) under the similar reaction conditions in good yield and single step reaction.

Corresponding author

Register with J-STAGE for free!