(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

HRID 490125ノート

反応式

HRID 490125 の反応式
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

参加物

4

反応物 2

HCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 178418287HCID 178418287、化合物2 回

生成物 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate収率 132.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

150 g of 1-tert-butyl 2-methyl(2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate, 264 g of pyridinium chlorochromate, and 75 g of celite were stirred in 2 L of chloroform at room temperature. During this stirring, another 100 g of pyridinium chlorochromate was added, and the reaction mixture was stirred for a total of 7 days. The reaction solution was filtered through celite (washed with 500 mL of chloroform), and the filtrate was concentrated under reduced pressure to obtain 197 g of black oil. The residue thus obtained was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/n-hexane=2/1; v/v) to obtain 119 g of the titled compound (yellow oily substance).

後処理

  1. filtrationThe reaction solution was filtered through celite (washed with 500 mL of chloroform)
  2. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-c1b9b4cce1f24942a441f3085e1994b5
出典データセット
uspto-grants-2009_05
特許番号
US07528124B2

反応ノート

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