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

HRID 2238474Notes

Reaction equation

HRID 2238474 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-fb4e4375d7dc4f358dfcdeee93f0ba31
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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