Sodium Benzoate → (2S,4S)-1-tert-Butyl 2-methyl 4-(benzoyloxy)pyrrolidine-1,2-dicarboxylate

HRID 257960

反応式

HRID 257960 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13]S(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([O-])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na+]>CS(C)=O.C(OCC)(=O)C>[C:22]([O:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:18]([O:20][CH3:21])=[O:19])[CH2:10]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 2

HCID 517055Sodium BenzoateHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 10760219(2S,4S)-1-tert-Butyl 2-methyl 4-(benzoyloxy)pyrrolidine-1,2-dicarboxylate収率 88.8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of (2S,4R)-1-t-butoxycarbonyl-4-methylsulfonyloxy-2-methoxycarbonylpyrrolidine (32.3 g) and sodium benzoate (28.8 g) in dimethyl sulfoxide (320 ml) was stirred at 90° C. overnight and cooled to room temperature. The mixture was diluted with ethyl acetate (600 ml) and washed successively with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The oil was crystallized from n-hexane to give (2S,4S)-4-benzoyloxy-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine (31.0 g) as a colorless crystal.

後処理

  1. temperaturecooled to room temperature
  2. washwashed successively with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil
  6. customThe oil was crystallized from n-hexane

出典と根拠

ORDレコード
ord-0d753ae9b80e49ffb6c8cf7cecf50bdb
出典データセット
uspto-grants-1993_11
特許番号
US05264453

関連ノート

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