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

HRID 988597Notes

Reaction equation

HRID 988597 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-7fc021bc7cd244c09fe7d87b6a1b1ecd
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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