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

HRID 344695노트

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HRID 344695 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 14824832(2S)-1-benzoylpyrrolidin-2-al수율 99.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

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온도
-70 °C

실험 절차

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:

후처리

  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)

출처 및 근거

ORD 기록
ord-acf436e7271d4b659fd7d1e0b8df29cd
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053414

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