1-(Diphenylmethyl)azetidin-3-one → 1-Benzhydryl-3-methylazetidin-3-ol

HRID 222322노트

반응식

HRID 222322 반응식
[CH3:1][Mg]I.[C:4]1([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]2[CH2:14][C:13](=[O:15])[CH2:12]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(OCC)C>[C:16]1([CH:10]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:11]2[CH2:14][C:13]([CH3:1])([OH:15])[CH2:12]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

4

반응물 2

HCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 102439891-Benzhydryl-3-methylazetidin-3-ol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

Methyl magnesium iodide (3M in diethyl ether, 1.4 mL, 4.2 mmol) was added dropwise to an ice-cold solution of 1-(diphenylmethyl)-3-azetidinone (1 g, 4.20 mmol) in diethyl ether (25 mL) and the mixture was stirred for 1 hour at 0° C. The crude reaction mixture was then purified directly by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 95:5, to afford the title compound the title compound as a pale yellow oil in 68% yield, 730 mg. 1H NMR (CDCl3, 400 MHz) δ: 1.54 (s, 3H), 3.02 (m, 2H), 3.22 (m, 2H), 4.39 (s, 1H), 7.20 (m, 4H), 7.26 (m, 4H), 7.41 (m, 2H); LRMS ESI+ m/z 254 [M+H]+

후처리

  1. customThe crude reaction mixture
  2. customwas then purified directly by column chromatography on silica gel
  3. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-35d7b925ab3e4019baa5591dbc185372
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207198B2

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