Benzyl Bromide → Ethyl 1-benzyl-3-methyl-2-oxo-4-pyrrolidinecarboxylate

HRID 580561Notes

Reaction equation

HRID 580561 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][NH:6][C:5]1=[O:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1>[CH2:15]([N:6]1[CH2:7][CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]([CH3:3])[C:5]1=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 122924633-Pyrrolidinecarboxylic acid, 4-methyl-5-oxo-, ethyl ester

Product 1

HCID 13933133Ethyl 1-benzyl-3-methyl-2-oxo-4-pyrrolidinecarboxylateYield 80.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of sodium hydride (2.30 g) in absolute dioxane (100 ml) was added dropwise ethyl 3-methyl-2-oxo-4-pyrrolidinecarboxylate (13.68 g) with stirring at room temperature. After stirring for 30 minutes, to a reaction mixture was added benzylbromide (16.42 g) during 20 minutes, then stirred for 2 hours and allowed to stand overnight at room temperature. The reaction mixture was poured into ice-water (100 ml) and extracted with chloroform, washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by vacuum distillation to give ethyl 1-benzyl-3-methyl-2-oxo-4-pyrrolidinecarboxylate (16.86 g), bp 155°-185° C./2 mmHg.

Workup

  1. stirringAfter stirring for 30 minutes, to a reaction mixture
  2. stirringstirred for 2 hours
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-8c8038e0da9e497b87dd3f02971af5a3
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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