m-Chloroperbenzoic acid → (2alpha,3alpha)-2,3-Epoxyandrostan-17-one

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Reaction Conditions

Reaction Steps

To a solution of compound 2 (320 mg, 1.17 mmol) in anhydrous dichloromethane (25 mL) was added m-CPBA (316 mg, 1.41 mmol) at 0° C. under an atmosphere of argon. The solution was stirred at 0° C. for 3 h. The solution was then 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/EtOAc: 8:2) to yield compound 22 (260 mg, 78%). 1H NMR (CDCl3) δ: 0.79 (s, 18-CH3), 0.85 (s, 19-CH3), 0.60-2.11 (residual CH and CH2), 2.43 (dd, J1=18.8 Hz, J2=8.7 Hz, 16β-H), 3.12 (t, J=5.8 Hz, 2×CH of epoxide), 3.16 (broad, s, 2×CH of epoxide).

Provenance & Evidence