Hydrochloric Acid → HCID 70207149, compound

HRID 1378390Notes

Reaction equation

HRID 1378390 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 11066560HCID 11066560, compound

Product 1

HCID 70207149HCID 70207149, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-123c7ab2243349d88a1d6466ec948d76
Source dataset
uspto-grants-1997_09
Patent number
US05668147

Reaction notes

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