Selective catalytic reduction of 7-methyl-6-dehydrotestosterone acetate to 7 beta-methyltestosterone acetate by benzyl alcohol. |
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Authors: | W H Chiu M E Wolff |
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Affiliation: | Department of Pharmaceutical Chemistry, School of Pharmacy University of California, San Francisco, California 94143 USA |
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Abstract: | Using benzyl alcohol as a hydrogen donor in the presence of Pd on charcoal, 7-methyl-6-dehydrotestosterone acetate was selectively reduced to 7 beta-methyltestosterone acetate in 90% yield. The addition of hydrogen atoms to the 6, 7 double bond proceeded from the less hindered alpha-face of the steroid molecule, giving rise to the 7 beta-methyl product. Gas chromatograph analysis indicated small amounts of the 7 alpha-methyl epimer, 7 beta-methyl-5 alpha-dihydrotestosterone acetate and the 5 beta-epimer. The 6,7 double bond was hydrogenated in preference to 4,5 double bond, although both are trisubstituted. |
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