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

HRID 1081691Notes

Reaction equation

HRID 1081691 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-3fd37743d93544b5b114db0b81e69261
Source dataset
uspto-grants-1996_12
Patent number
US05587386

Reaction notes

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