1-(tert-butyl) 2-methyl (2S)-4-hydroxypyrrolidine-1,2-dicarboxylate → 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

HRID 345323ノート

反応式

HRID 345323 の反応式
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][CH:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11]

参加物

5

反応物 2

HCID 121855781-(tert-butyl) 2-methyl (2S)-4-hydroxypyrrolidine-1,2-dicarboxylateHCID 178418287HCID 178418287、化合物

生成物 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 12.7 g of N-t-butoxycarbonyl-4-hydroxyproline methyl ester and 44.7 g of pyridinium chlorochromate in 150 ml of methylene chloride is stirred at room temperature for 30 hours, diluted with 200 ml of ether and filtered through Florisil washing with ether (500 ml). The solution is evaporated to dryness, the residue is purified by flash chromatography on silica gel using ethyl acetate/hexane (40:60) as eluant to give N-t-butoxycarbonyl-4-oxoproline methyl ester.

後処理

  1. filtrationfiltered through Florisil washing with ether (500 ml)
  2. customThe solution is evaporated to dryness
  3. customthe residue is purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-7651f837810747ccb6f2c7b226788bfa
出典データセット
uspto-grants-1991_10
特許番号
US05057506

反応ノート

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