Sodium Carbonate → 1-Benzyl-5-methylpyrrolidin-3-one

HRID 2299107Notes

Reaction equation

HRID 2299107 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[CH:10](C(OCC)=O)[CH:9]1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.S(=O)(=O)(O)O>[CH2:1]([N:8]1[CH:9]([CH3:19])[CH2:10][C:11](=[O:13])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 18379061Ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylate

Product 1

HCID 183793251-Benzyl-5-methylpyrrolidin-3-oneYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylate (3.4 g, 13 mmol) in water (95 ml) and sulfuric acid (5 ml) was heated to 90° C. overnight. The mixture was allowed to cool was neutralized with sodium carbonate, extracted with methylene chloride. The combined organic layer filtered through a plug of silica gel and concentrated to give 1-benzyl-5-methyl-3-pyrrolidinone (1.13 gm, 46%) as a yellow oil, MS (M+H)+=190.

Workup

  1. temperatureto cool
  2. extractionextracted with methylene chloride
  3. filtrationThe combined organic layer filtered through a plug of silica gel
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab382e98e778498cb3b798c280a69d67
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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