Hydrochloric Acid → HCID 70207149、化合物

HRID 1378390ノート

反応式

HRID 1378390 の反応式
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([F:14])([F:13])[F:12])[CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].Cl.C(=O)(O)[O-].[Na+].[CH2:28]([O:35][C:36](Cl)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)C.[C].[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([F:14])([F:12])[F:13])[CH2:9][N:8]([C:36]([O:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:37])[CH2:7]1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 11066560HCID 11066560、化合物

生成物 1

HCID 70207149HCID 70207149、化合物収率 92.3%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

In 150 ml of ethanol, is dissolved 15.0 g (49.8 mmol) of trans-1-benzyl-4-trifluoromethylpyrrolidine-3-carboxylic acid ethyl ester. To the above solution, are added 6 ml of conc-hydrochloride and then 3 g of 10% palladium carbon. The mixture is stirred at 40° C. and 1 atmospheric pressure to perform a hydrogenation. Four hours later, the catalyzer is removed by filtration. The filtrate is concentrated under reduced pressure, and the residue was dissolved in 60 ml of water. To the solution, is added 11 g (131 mmol) of sodium bicarbonate. Further, 10.2 g (59.8 mmol) of benzylchloroformate is added to the above solution on cooling with ice. The mixture is stirred at 0° C. for 1 hour and then at room temperature for 11 hours. The reaction mixture is extracted with 150 ml of diethyl ether. The organic phase is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The dried organic phase is concentrated under reduced pressure. The residue was purified with silica gel column chromatography (elusion solvent; n-hexane/ethyl acetate (10/1→5/1)) to give 15.87 g of the objective substance as a colorless oily matter (yield 92.3%).

後処理

  1. customFour hours later, the catalyzer is removed by filtration
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 60 ml of water
  4. temperatureon cooling with ice
  5. stirringThe mixture is stirred at 0° C. for 1 hour
  6. extractionThe reaction mixture is extracted with 150 ml of diethyl ether
  7. washThe organic phase is washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe dried organic phase is concentrated under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (elusion solvent; n-hexane/ethyl acetate (10/1→5/1))
  11. customto give 15.87 g of the objective substance as a colorless oily matter (yield 92.3%)

出典と根拠

ORDレコード
ord-123c7ab2243349d88a1d6466ec948d76
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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