Water → [(1-Benzylpyrrolidin-3-yl)methyl](2,2,2-trifluoroethyl)amine

HRID 620850Notes

Reaction equation

HRID 620850 reaction equation
O=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14]([NH:16][CH2:17][C:18]([F:21])([F:20])[F:19])=O)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:8]1([CH2:7][N:6]2[CH2:2][CH2:3][CH:4]([CH2:14][NH:16][CH2:17][C:18]([F:21])([F:19])[F:20])[CH2:5]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 134917961-benzyl-5-oxo-N-(2,2,2-trifluoroethyl)pyrrolidine-3-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 14280884[(1-Benzylpyrrolidin-3-yl)methyl](2,2,2-trifluoroethyl)amineYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 8.50 g (28.3 mole) of 5-oxo-1-(phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinecarboxamide in 100 ml tetrahydrofuran was added dropwise to 3.22 g (84.9 mmole) of lithium aluminum hydride in 50 ml tetrahydrofuran. The reaction was refluxed two hours, then stirred at room temperature overnight. The reaction was cooled in an ice bath and 3.2 ml of water, 3.2 ml of 15% sodium hydroxide, and 9.6 ml of water were added. The precipitated salts were filtered and washed with hot ethanol. The combined filtrates were concentrated under reduced pressure. The residue was taken up in dichloromethane, filtered, and dried over magnesium sulfate. The solvent was removed at reduced pressure to give 7.15 g of 1-(phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinemethanamine.

Workup

  1. temperatureThe reaction was refluxed two hours
  2. temperatureThe reaction was cooled in an ice bath
  3. filtrationThe precipitated salts were filtered
  4. washwashed with hot ethanol
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. filtrationfiltered
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-0d95285ff9534bf39d2b4e4093cff447
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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