Hydrochloric Acid → Ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylate

HRID 2299106Notes

Reaction equation

HRID 2299106 reaction equation
CC(C)([O-])C.[K+].C1COCC1.[CH2:12]([N:19]([CH2:28][C:29]([O:31]C)=O)[CH:20]([CH3:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:12]([N:19]1[CH2:28][C:29](=[O:31])[CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]1[CH3:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 18379207Ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18379061Ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylateYield 83.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium t-butoxide 1N in THF (17.5 ml, 17.5 mmol) was added to an ice cooled solution of ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoate (4.6 g, 15.6 mmol) in toluene (30 ml). The reaction was allowed to warm to room temperature and stir overnight. To this 1 N HCl (30 ml) was added, the reaction was stirred for 8 h, was neutralized with sodium carbonate and extracted with methylene chloride (3×75 ml). The combined organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylate (3.4 g, 83%) as an oil, MS (M+H)+=262.

Workup

  1. stirringthe reaction was stirred for 8 h
  2. extractionextracted with methylene chloride (3×75 ml)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b9d1db597ed24f059657f13487c5aec4
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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