m-Chloroperbenzoic acid → HCID 86660494, 화합물

HRID 244248

반응식

HRID 244248 반응식
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH:13]=[CH:12][CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20].C1C=C(Cl)C=C(C(OO)=[O:29])C=1>ClCCl>[O:29]1[C@H:12]2[CH2:11][CH:10]3[C@:15]([CH3:16])([CH2:14][C@@H:13]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[C:3](=[O:20])[CH2:4][CH2:5]2)[CH2:8][CH2:9]3

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 1019285alpha-Androst-2-en-17-one

생성물 1

HCID 86660494HCID 86660494, 화합물수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  1. washwashed with an aqueous sodium bicarbonate solution (10%)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe crude compound was purified by flash chromatography (Hexanes/EtOAc: 8:2)

출처 및 근거

ORD 기록
ord-2b7ec160332042a69b0aac988bc41c04
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653054B2

연결된 노트

불러오는 중…