Sodium borohydride (0.013 g) was added to a solution of (7α,17β)-7-ethyl-17-hydroxyestr-5(10)en-3-one (Example 2; 0.25 g) in a mixture of tetrahydrofuran (4.2 ml) and methanol (4.2 ml). The reaction mixture was stirred at room temperature for 2 h and then quenched with acetone. The mixture was poured into water and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. Column chromatography afforded (3α,7α,17β)-7-ethylestr-5(10)-ene-3,17-diol, m.p. 98-100° C., and (3β,7α,17β)-7-ethylestr-5(10)-ene-3,17-diol, m.p. 60-65° C.
