Potassium Carbonate → HCID 66910196, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3β,17β-di(dimethyltert-butylsilyloxy)-6α-acetoxyandrostane and 3α,17β-di(dimethyltert-butylsilyloxy)-6α-acetoxyandrostane (90/10 mixture, 7.58 g) in MeOH/dioxane 1/4 (100 mL), K2CO3 (896 mg) was added. After stirring for 72 h at 40° C., the mixture was quenched by addition of H2O. The organic solvents were evaporated and the concentrated solution was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness to give 3β,17β-di(dimethyltert-butylsilyloxy)androstane-6α-ol and 3α,17β-di(dimethyltert-butylsilyloxy)androstane-6α-ol (90/10 mixture, 6.30 g, 85%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.30 (bb, 1H), 3.55 (bb, 1H), 3.47 (m, 1H), 2.05 (bb, 1H), 1.92-1.73 (m, 2H), 1.68-0.87 (m, 17H), 0.84 (s, 18H), 0.72 (s, 3H), 0.62 (s, 3H), 0.56 (m, 1H), 0.02 (s, 3H), 0.01 (s, 6H), 0.01 (s, 3H).

Provenance & Evidence