Dimethyl Sulfoxide → (3S)-3-Formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917358ノート

反応式

HRID 1917358 の反応式
[C:1]([O:5][C:6]([C@@:8]1([CH2:22][OH:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(C)=O>ClCCl>[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[O:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57758657HCID 57758657、化合物

生成物 1

HCID 86664650(3S)-3-Formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester収率 71.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(3S)-3-Hydroxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (4.0 g, 12.52 mmol) was dissolved in dichloromethane. Triethylamine (6.34 g, 62.62 mmol), dimethyl sulfoxide (3.91 g, 50.09 mmol), and a SO3-pyridine complex (3.99 g, 25.05 mmol) were sequentially added at 0° C., and the mixture was stirred for 17 hours. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (60% ethyl acetate/hexane) to give 2.85 g of the title compound as a colorless solid.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-8c1b0496ce684e3f98bd63c1da025d78
出典データセット
uspto-grants-2013_12
特許番号
US08618094B2

反応ノート

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