Selective catalytic reduction of 7-methyl-6-dehydrotestosterone acetate to 7 beta-methyltestosterone acetate by benzyl alcohol.
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.
D001592:Benzyl Alcohols; D055598:Chemical Phenomena; D002621:Chemistry; D013196:Dihydrotestosterone / Q000031:analogs & derivatives*; D008722:Methods; D008777:Methyltestosterone / Q000138:chemical synthesis* / Q000031:analogs & derivatives; D010084:Oxidation-Reduction
C021709:7-methyl-6-dehydrotestosterone acetate; D001592:Benzyl Alcohols; D013196:Dihydrotestosterone; D008777:Methyltestosterone