Efficient Oxidizing Methods for the Synthesis of Oxandrolone Intermediates

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概要

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• 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 ℃, sodium hypochlorite and H_2O_2/Na_2WO_4 under phase transfer conditions to give 17β-hydroxy-17α-methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H_2O_2/Na_2WO_4/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-Δ^1-androsten-3-one (3) under the similar reaction conditions in good yield and single step reaction.

• 公益社団法人日本薬学会の論文
• 2004-08-01

著者

• Tandon V

  Medical Chemistry Research Laboratory Dr. B. R. Ambedkar Center For Biomedical Research University O

• Chandra Ramesh

  Medical Chemistry Research Laboratory Dr. B. R. Ambedkar Center For Biomedical Research University O

• GINOTRA Sandeep

  Medical Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University

• CHHIKARA Bhupender

  Medical Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University

• SINGH Manish

  Medical Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University

• TANDON Vibha

  Medical Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University

• Singh Manish

  Medical Chemistry Research Laboratory Dr. B. R. Ambedkar Center For Biomedical Research University O

• Ginotra Sandeep

  Medical Chemistry Research Laboratory Dr. B. R. Ambedkar Center For Biomedical Research University O

• Chhikara B

  Medical Chemistry Research Laboratory Dr. B. R. Ambedkar Center For Biomedical Research University O

関連論文

• Efficient Oxidizing Methods for the Synthesis of Oxandrolone Intermediates

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