Dimethyl Sulfoxide → 1-(Diphenylmethyl)azetidin-3-one

HRID 83080

反応式

HRID 83080 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]([N:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:11]([N:24]1[CH2:27][C:26](=[O:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

生成物 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one収率 105%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a stirring solution of DMSO (12.45 ml, 176 mmol) in DCM (150 mL) at −78° C. under an argon atmosphere was added dropwise oxalyl chloride (8.61 mL, 100 mmol). After stirring for 30 minutes at −78° C., a solution of 1-benzhydrylazetidin-3-ol (20 g, 84 mmol) in DCM (75 mL) was added dropwise. The reaction mixture was stirred for 1 h at −78° C. before triethylamine (58.2 ml, 418 mmol) was added. The reaction mixture was allowed to reach 0° C. and was quenched with saturated NH4Cl (150 mL), and then extracted with DCM (3×). The combined organic layers were washed with water, brine, dried on Na2SO4 and concentrated to give crude 1-benzhydrylazetidin-3-one (20.8 g, 105%) as a yellow solid.

後処理

  1. additionwas added
  2. customto reach 0° C.
  3. customwas quenched with saturated NH4Cl (150 mL)
  4. extractionextracted with DCM (3×)
  5. washThe combined organic layers were washed with water, brine
  6. customdried on Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a7909c04f97a469f95746b8e35291831
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

関連ノート

読み込み中…