m-Chloroperbenzoic acid → (2alpha,3alpha,17beta)-17-Methoxy-2,3-epoxyandrostane

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Reaction Conditions

Reaction Steps

To a solution of compound 34 (160 mg, 0.55 mmol) in anhydrous dichloromethane (10 mL) was added m-CPBA (149 mg, 0.67 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: 9:1) to yield compound 35 (127 mg, 75%). 1H NMR (CDCl3) δ: 0.73 (s, 18-CH3), 0.76 (s, 19-CH3), 0.58-2.05 (residual CH and CH2), 3.12 and 3.15 (2 m, 2×CH of epoxide), 3.21 (t, J=8.2 Hz, 17α-CH), 3.34 (s, OCH3).

Provenance & Evidence