1,4-Dioxane → HCID 68132020, compound

Participants

Reaction Steps

To 0.83 g. of 1,4,6-androstatriene-3,17-dione in 15 ml. of dioxane and 0.83 ml. of pyridine add 0.75 g. of osmium tetroxide. Stir the reaction mixture under an atmosphere of nitrogen at room temperature in the absence of light for two days. Isolate the resultant product in a manner similar to that described in Example 1B. Purify by chromatographing on thin layer plates developing with ethyl acetate-chloroform-methanol (4.5:4.5:1). Combine like fractions, elute with ethyl acetate, and evaporate the eluate to a residue comprising 6β,7β-dihydroxy-1,4-androstadiene-3,17-dione. Yield=445 mg. (48% theory). Further purify by recrystallization from methanol; [α]D26° +66.7° (acetone); λmaxmethanol 244 nm (γ=15,300); n.m.r. (dmso-d6 /D2O) δ0.89 (C13 -CH3); 1.37 (C10 -CH3); 3.25(7α-H; d,d J10,3Hz); 4.24 (6α-H; d,J 3.5Hz); 6.11 (C4 -H; d,J 2Hz); 6.11 (C2 -H; d,d J10,2Hz); 7.18 (C1H; d,J 10Hz).

Provenance & Evidence