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

HRID 244254Notes

Reaction equation

[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[CH:12]([CH2:13][CH:14]=[CH:15][CH2:16]1)[CH2:11][CH2:10]3.C1C=C(Cl)C=C(C(OO)=[O:30])C=1>ClCCl>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[CH:12]([CH2:13][C@@H:14]2[O:30][C@@H:15]2[CH2:16]1)[CH2:11][CH2:10]3

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

washwashed with an aqueous sodium bicarbonate solution (10%)
dry with materialThe organic layer was dried with sodium sulfate
customevaporated under reduced pressure
customThe crude compound was purified by flash chromatography (Hexanes/acetone: 9:1)

Sources & evidence

ORD record: ord-f618dd93a59a4beea0e062eb1324f1dc
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653054B2

Reaction notes

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