Methanol → (S)-1-isopropyl-5-oxopyrrolidine-2-carboxylic acid

HRID 2238477Notes

Reaction equation

HRID 2238477 reaction equation
[CH3:1][CH:2]([N:4]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:5]1[C:6]([O:8]C)=[O:7])[CH3:3].CO.[OH-].[Na+]>O>[CH3:3][CH:2]([N:4]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:5]1[C:6]([OH:8])=[O:7])[CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67461795methyl (2S)-5-oxo-1-(propan-2-yl)pyrrolidine-2-carboxylate

Product 1

HCID 18649401(S)-1-isopropyl-5-oxopyrrolidine-2-carboxylic acidYield 42.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 1-(1-methylethyl)-5-oxo-prolinate (0.152 g, 0.82 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 for ˜4 hrs 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 1-(1-methylethyl)-5-oxo-proline (0.060 g) as a yellow oil which crystallized on standing.

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-17cd0fa115224fcaaa4e28bbca942dee
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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