Sodium Hydroxide → L-Proline, 1-ethyl-5-oxo-

HRID 2238487Notes

Reaction equation

HRID 2238487 reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[CH2:10][CH2:9][C@H:4]1[C:5]([O:7]C)=[O:6])[CH3:2].[OH-].[Na+]>CO>[CH2:1]([N:3]1[C:11](=[O:12])[CH2:10][CH2:9][C@H:4]1[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67459238Methyl (2S)-1-ethyl-5-oxopyrrolidine-2-carboxylate

Product 1

HCID 18605196L-Proline, 1-ethyl-5-oxo-Yield 15.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-ethyl-5-oxo-prolinate (1.91 g, 11.17 mmol) was dissolved in methanol (25 ml) and treated with 2M aqueous sodium hydroxide (7.3 ml, 14.52 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 a clear oil which crystallized on standing. Trituration with hexane and ether and drying gave pure 1-ethyl-5-oxo-proline (0.271 g) as a white solid.

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
  7. customto give a clear oil which
  8. customcrystallized
  9. dry with materialTrituration with hexane and ether and drying

Sources & evidence

ORD record
ord-73fd3d4d607146fc9e2340b1be239f6a
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Reaction notes

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