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R. I. Dorfman1 has recently found that the diacetate of 4-androstene-3/3(or a) 17/3-diol was a highly potent long acting androgen, comparable in activity to testosterone esters. This observation was of some interest in view of the finding of Butenandt and coworkers2 that the parent compound, 4-androstene-3/3,17/3-diol,3 exhibited very little activity in the capon comb test. In view of the work by Dorfman which indicated that hormone activity could be maintained with a 4 5-3-1 grouping in the molecule, it was decided to prepare the unknown 17a-methyl-4-androstene-3/3,17/3-diol (Ila) for a comparative study of its androgenic activity especially with methyl testosterone (I) and 17a-methyI-5-androstene-3/3,17/3-diol.Methyl testosterone (I) on reduction with sodium borohydride4 in methanol-ethyl acetate gave in 70% yield 17a-methyI-4-androstene-3/3,17/3-diol (Ila), which was isolated and purified by crystallization directly from the reduction mixture. The /3-configuration at C3 was assigned on the basis of digitonide formation. The digitonide on decomposition with pyridine gave back the 3/3,17/3-diol Ila identical with the starting material. This established that the product Ila was not contaminated with the chemically possible 3a,17/3-diol. The presence of the latter in the purification mother liquors was not investigated.The 3-acetate lib and 3-propionate lie were prepared in the usual manner.