Methanol → Methyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate

HRID 1246698Notes

Reaction equation

HRID 1246698 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:22]O>>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH3:22])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3228021-Benzyl-5-oxopyrrolidine-2-carboxylic acid

Product 1

HCID 11096495Methyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate

Procedure

1-Benzyl-5-oxo-2-pyrrolidinecarboxylic acid (9.69 g, 44.2 mmol) in methanol (75 mL) was treated with sulfuric acid (0.5 mL) and refluxed for 2.5 hours. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The ethyl acetate phase was concentrated under reduced pressure to provide the title compound which was used in the next step without further purification.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. concentrationThe ethyl acetate phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2f0097f0e8ae4509ae23b521ccd05b96
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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