Sodium Hydroxide → rac-(3R,4R)-1-((benzyloxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-3-carboxylic acid

HRID 1378391ノート

反応式

HRID 1378391 の反応式
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([F:14])([F:13])[F:12])[CH2:9][N:8]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:18]([O:17][C:15]([N:8]1[CH2:9][C@@H:10]([C:11]([F:12])([F:13])[F:14])[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 70207149HCID 70207149、化合物

生成物 1

HCID 70207030rac-(3R,4R)-1-((benzyloxy)carbonyl)-4-(trifluoromethyl)pyrrolidine-3-carboxylic acid収率 95.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

In 92 ml of ethanol, is dissolved 15.8 g (45.8 mmol) of trans-1-benzyloxycarbonyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester. To the above solution, is added 46 ml of 2N sodium hydroxide on cooling with ice. The mixture is stirred at 0° C. for 1 hour and then concentrated under reduced pressure. The residue is dissolved in 100 ml of water. The solution is washed with diethyl ether. The water phase is adjusted to pH 3 with citric acid. The solution is extracted twice with dichloromethane. The organic phases were put together and dried over anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure to give 13.84 g of the objective substance as a colorless powder (yield 95.3%).

後処理

  1. temperatureon cooling with ice
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue is dissolved in 100 ml of water
  4. washThe solution is washed with diethyl ether
  5. extractionThe solution is extracted twice with dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe dried organic phase was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-1666cf2ab13b4a7c8878f9347eab5387
出典データセット
uspto-grants-1997_09
特許番号
US05668147

反応ノート

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