Methanol → (S)-1-Benzyl-5-carboxy-2-pyrrolidinone

HRID 554068Notes

Reaction equation

HRID 554068 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]([O:16]C)=[O:15])[CH2:4][CH2:3]1.CO.[OH-].[Na+]>O>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:5]([C:14]([OH:16])=[O:15])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 10998904(S)-Methyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

Product 1

HCID 10900113(S)-1-Benzyl-5-carboxy-2-pyrrolidinoneYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-oxo-1-(phenylmethyl)-prolinate (0.212 g, 0.91 mmol) was dissolved in water (3 ml) and methanol (0.5 ml) and treated with 2M aqueous sodium hydroxide (0.682 ml, 1.36 mmol). The mixture was stirred overnight at room temperature and then washed with dichloromethane. The aqueous layer was evaporated and the residue treated with an excess of 1M hydrogen chloride in ether (˜5 ml). The mixture was evaporated once more and the residue was triturated with dichloromethane. The solid material was discarded and the combined dichloromethane fractions were evaporated to give 5-oxo-1-(phenylmethyl)-proline (0.182 g) as a yellow oil which was used without further purification.

Workup

  1. washwashed with dichloromethane
  2. customThe aqueous layer was evaporated
  3. additionthe residue treated with an excess of 1M hydrogen chloride in ether (˜5 ml)
  4. customThe mixture was evaporated once more
  5. customthe residue was triturated with dichloromethane
  6. customthe combined dichloromethane fractions were evaporated

Sources & evidence

ORD record
ord-47f701127b2943ddbc9e5b5968f2c3c3
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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