Aluminium lithium hydride → N,N-dimethyl-1-[(2S)-1-(phenylmethyl)-2-pyrrolidinyl]methanamine

HRID 1366668Notes

Reaction equation

HRID 1366668 reaction equation
[CH3:1][N:2]([CH3:18])[C:3](=O)[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][N:2]([CH3:18])[CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 669362321-benzoyl-N,N-dimethylpyrrolidine-2-carboxamide

Product 1

HCID 66936141N,N-dimethyl-1-[(2S)-1-(phenylmethyl)-2-pyrrolidinyl]methanamineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Dimethyl-1-(phenylcarbonyl)-L-prolinamide (4.50 g, 18.269 mmol) was dissolved in 100 mL of THF, cooled to 0° C., and then LiAlH4 (1.386 mg, 36.54 mmol) was added portion wise. The mixture was heated to 80° C. for 2 h, then allowed to cool to RT. The reaction was quenched in succession with H2O (1.5 mL), 15% aq. NaOH (1.5 mL) and H2O (4.5 mL) and was stirred at room temperature overnight. The contents were filtered, and the filtrate was concentrated in vacuo to provide N,N-dimethyl-1-[(2S)-1-(phenylmethyl)-2-pyrrolidinyl]methanamine (3.7305 g, 94%). LCMS: (M+H)+: 219.1.

Workup

  1. temperatureThe mixture was heated to 80° C. for 2 h
  2. temperatureto cool to RT
  3. customThe reaction was quenched in succession with H2O (1.5 mL), 15% aq. NaOH (1.5 mL) and H2O (4.5 mL)
  4. filtrationThe contents were filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ee2c575ae0ff4c62b57c53951b856980
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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