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

HRID 244252Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

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: 95:5)

Sources & evidence

ORD record: ord-07c11c91cb6241378715919f12d3c029
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653054B2

Reaction notes

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