Ethanol → (+/-)-1-Benzyl-4-methyl-5-oxo-3-pyrrolidinecarboxylic acid

HRID 1445268Notes

Reaction equation

HRID 1445268 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]([CH3:14])[CH:10]([C:15]([O:17]CC)=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+]>O>[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]([CH3:14])[CH:10]([C:15]([OH:17])=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13933133Ethyl 1-benzyl-3-methyl-2-oxo-4-pyrrolidinecarboxylate

Product 1

HCID 19354246(+/-)-1-Benzyl-4-methyl-5-oxo-3-pyrrolidinecarboxylic acidYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.13 g of ethyl 1-benzyl-4-methyl-5-oxo-3-pyrrolidinecarboxylate (42, cf. JP-A-62-4284), 40 ml of 50% ethanol, and 2 g of sodium hydroxide was stirred at room temperature for 42 hours. To the reaction mixture was added 100 ml of water, and the mixture was washed with chloroform. The aqueous layer was neutralized with hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 3.40 g of (±)-1-benzyl-4-methyl-5-oxo-3-pyrrolidinecarboxylic acid (43) as a colorless crystal.

Workup

  1. washthe mixture was washed with chloroform
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e8470847997f4cd2ab0d1eaa6f5fe1aa
Source dataset
uspto-grants-2010_02
Patent number
USRE041149E1

Reaction notes

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