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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
8
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pubmed:dateCreated |
2004-8-12
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pubmed:abstractText |
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.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
0009-2363
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:volume |
52
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
989-91
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:15304998-Androstane-3,17-diol,
pubmed-meshheading:15304998-Benzoic Acid,
pubmed-meshheading:15304998-Chlorine,
pubmed-meshheading:15304998-Dihydrotestosterone,
pubmed-meshheading:15304998-Iodine,
pubmed-meshheading:15304998-Models, Chemical,
pubmed-meshheading:15304998-Oxandrolone,
pubmed-meshheading:15304998-Oxidation-Reduction,
pubmed-meshheading:15304998-Sodium Hypochlorite
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pubmed:year |
2004
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pubmed:articleTitle |
Efficient oxidizing methods for the synthesis of oxandrolone intermediates.
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pubmed:affiliation |
Medicinal Chemistry Research Laboratory, Dr. B. R. Ambedkar Center for Biomedical Research, University of Delhi, Dehli, India.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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