m-Chloroperbenzoic acid → (2alpha,3alpha,17beta)-17-Methyl-2,3-epoxyandrostan-17-ol

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Reaction Conditions

Reaction Steps

To a solution of compound 27 (120 mg, 0.43 mmol) in anhydrous dichloromethane (10 mL) was added m-CPBA (112 mg, 0.54 mmol) at 0° C. under an atmosphere of argon. The solution was stirred at 0° C. over a period of 3 h. The solution was subsequently diluted with dichloromethane (50 mL) and washed with an aqueous sodium bicarbonate solution (10%). The organic layer was dried with sodium sulfate and evaporated under reduced pressure. The crude compound was purified by flash chromatography (Hexanes/acetone: 95:5) to yield compound 28 (116 mg, 91%). 1H NMR (CDCl3) δ: 0.77 (s, 19-CH3), 0.83 (s, 18-CH3), 1.21 (s, 17α-CH3), 0.60-1.95 (residual CH and CH2), 3.11 (t, J=5.8 Hz, CH of epoxide) and 3.15 (broad s, 2×CH of epoxide).

Provenance & Evidence