Dimethyl Sulfoxide → (2S)-1-benzoylpyrrolidin-2-al

HRID 344695ノート

反応式

HRID 344695 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][OH:25])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH:24]=[O:25])(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 128307942-Pyrrolidinemethanol, 1-benzoyl-, (2S)-

生成物 1

HCID 14824832(2S)-1-benzoylpyrrolidin-2-al収率 99.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-70 °C

実験手順

A solution of DMSO (27.9 ml) in methylene chloride (50 ml) was added to a solution of oxalyl chloride (16.4 ml) in methylene chloride (300 ml) which was cooled to -70° C. A solution of (2S)-1-benzoylpyrrolidine-2-methanol (24.1 g) in methylene chloride (120 ml) was added dropiwise to the solution at -70° C. The mixture was stirred for 30 mins. Triethylamine (89.5 ml) was added dropwise to the reaction solution at -70° C. The mixture was stirred for 50 mins at the same temperature, and then rised to 0° C. gradually. Water was added to the solution. The mixture was extracted with methylene chloride. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (23.7 g) having the following physical data:

後処理

  1. stirringThe mixture was stirred for 50 mins at the same temperature
  2. customrised to 0° C.
  3. extractionThe mixture was extracted with methylene chloride
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

出典と根拠

ORDレコード
ord-acf436e7271d4b659fd7d1e0b8df29cd
出典データセット
uspto-grants-1991_10
特許番号
US05053414

反応ノート

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