Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate → (1-Benzylpyrrolidin-3-yl)methanol

HRID 2300806Notes

Reaction equation

HRID 2300806 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:18](=O)[CH2:17][CH:16]([C:20](OC)=[O:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([CH2:20][OH:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5176654(1-Benzylpyrrolidin-3-yl)methanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.50 g of lithium aluminum hydride in 35 mL of THF at 0° C. was added (dropwise via cannula) a solution of 2.00 g of methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate in 10 mL of THF. The cooling bath was removed and the mixture was stirred for 2.5 h at room temperature. The mixture was recooled to 0° C. and quenched by careful, sequential addition of 0.5 mL of water, 0.5 mL of 15% aqueous NaOH, and 1.5 mL of water. The mixture was stirred at room temperature for 1 h, at which point all solids were white, then filtered. The solids were washed thoroughly with Et2O, and the filtrate was dried over MgSO4 and concentrated to give 1.61 g of the title compound as a colorless oil.

Workup

  1. customThe cooling bath was removed
  2. customwas recooled to 0° C.
  3. customquenched by careful,
  4. additionsequential addition of 0.5 mL of water, 0.5 mL of 15% aqueous NaOH, and 1.5 mL of water
  5. stirringThe mixture was stirred at room temperature for 1 h, at which point all solids
  6. filtrationfiltered
  7. washThe solids were washed thoroughly with Et2O
  8. dry with materialthe filtrate was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-41362c80c7ce4750a2a227b013c59dba
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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