Lithium Hydroxide → 1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid

HRID 1269763Notes

Reaction equation

HRID 1269763 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]([O:16]C)=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].S([O-])(O)(=O)=O.[K+]>CO.O1CCCC1>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylateHCID 516920Potassium bisulfate

Product 1

HCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate (2.00 g, 8.57 mmol) was dissolved in a mixed solvent of methanol (10 ml) and tetrahydrofuran (10 ml), followed by adding thereto a 2N aqueous lithium hydroxide solution (8.6 ml, 17.2 mmol), and the resulting mixture was heated under reflux for 20 minutes. After completion of the reaction, the reaction solution was ice-cooled, made into an acidic solution with an aqueous potassium hydrogensulfate solution, and then extracted with ethyl acetate. The ethyl acetate layer was concentrated, washed by repulping (ethyl acetate/hexane), and then dried to obtain 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid (1.83 g, 97%).

Workup

  1. additionby adding
  2. temperatureunder reflux for 20 minutes
  3. customAfter completion of the reaction
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. concentrationThe ethyl acetate layer was concentrated
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-327fd0952ed04d898951a9f6721b6ccf
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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