Methyl 1-benzylpyrrolidine-3-carboxylate → (1-Benzylpyrrolidin-3-yl)methanol

HRID 1882926Notes

Reaction equation

HRID 1882926 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](OC)=[O:14])[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>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4610751Methyl 1-benzylpyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5176654(1-Benzylpyrrolidin-3-yl)methanolYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 1-benzylpyrrolidine-3-carboxylate (11.67 g, 50 mmol) and tetrahydrofuran, at 0° C. was added lithium aluminum hydride (3.795 g, 100 mmol). The reaction was warmed to room temperature and refluxed for 24 hours. After cooling to 0° C., the reaction was quenched with saturated sodium sulfate and warmed to room temperature. Tetrahyrofuran (50 mL) and solid sodium sulfate were added to the mixture. After stirring for 1 hour, the mixture was filtered and the filtrate was concentrated and vacuum dried for 3 days to give the title compound as a colorless oil (8.49 g, 88%).

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling to 0° C.
  3. customthe reaction was quenched with saturated sodium sulfate
  4. temperaturewarmed to room temperature
  5. additionTetrahyrofuran (50 mL) and solid sodium sulfate were added to the mixture
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated
  8. customvacuum dried for 3 days

Sources & evidence

ORD record
ord-378b333e2e1d48dca22eac20150ea4e6
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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