1-Benzyl-5-oxopyrrolidine-3-carboxamide → (1-Benzylpyrrolidin-3-yl)methanamine

HRID 1276360Notes

Reaction equation

HRID 1276360 reaction equation
[CH2:1]([N:8]1[C:12](=O)[CH2:11][CH:10]([C:14]([NH2:16])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:16][CH2:14][CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 52217541-Benzyl-5-oxopyrrolidine-3-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 3157467(1-Benzylpyrrolidin-3-yl)methanamineYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid amide (22 g, 0.1 mol) was added portionwise to a stirred solution of lithium aluminum hydride (9.5 g, 0.25 mol, 2.5 equiv.) in dry tetrahydrofuran (600 mL). After the initial effervescence had subsided, the reaction mixture was heated at reflux at room temperature for 24 h, at which time analysis of the reaction mixture by LCMS showed there was no starting material. The reaction mixture was quenched by dropwise addition of saturated sodium sulphate solution with stirring until no further effervescence was observed. The suspension was filtered through a celite plug, eluting with diethyl ether (200 mL). The solvent was remove to afford 3-(RS)-aminomethyl-1-benzylpyrrolidine as an oil (14.7 g) which was used directly without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. customThe reaction mixture was quenched by dropwise addition of saturated sodium sulphate solution
  3. filtrationThe suspension was filtered through a celite plug
  4. washeluting with diethyl ether (200 mL)
  5. customThe solvent was remove

Sources & evidence

ORD record
ord-034d0e5929f547feb8c3ecfdbd31cc90
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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