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

HRID 225805

反応式

HRID 225805 の反応式
[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

参加物

4

反応物 2

HCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418373HCID 178418373、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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]+

後処理

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

出典と根拠

ORDレコード
ord-231cf604f4ab4a5b920037b6a7f6c6a0
出典データセット
uspto-grants-2009_07
特許番号
US07557131B2

関連ノート

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