Methyl iodide → (+/-) 5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one

HRID 580055Notes

Reaction equation

HRID 580055 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:10][C:9](=[O:11])[CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].[H-].[Na+].[CH3:25]I>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:10]([CH3:25])[C:9](=[O:11])[CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 986274-Phenyl-5,5-dicarbethoxy-2-pyrrolidinone

Product 1

HCID 13825976(+/-) 5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-oneYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 100 g (0.33 mole) of (±) 5,5-diethoxycarbonyl-4-phenylpyrrolidin-2-one in 500 ml of absolute dimethylformamide was added dropwise to a suspension of 9.64 g (0.36 mole) of sodium hydride in 200 ml of absolute dimethylformamide at room temperature under an N2 atmosphere. The mixture was subsequently stirred at room temperature until the evolution of gas had ended, a solution of 93.7 g (0.66 mole) of methyl iodide in 50 ml of absolute dimethylformamide was then added and the mixture was stirred at room temperature until all the starting material had reacted (about 1 hour, thin layer chromatography check). The reaction mixture was poured into 2 l of buffer solution, pH=7, and extracted five times with 600 ml of diethyl ether each time. Drying of the organic extracts (MgSO4) and stripping off of the solvent in vacuo gave 105 g (99.6%) of the title compound (95% pure according to the 1H-NMR spectrum), which was further reacted directly. A sample was distilled in a bulb tube (boiling point0.5 : 240° C.) for analysis, Rf : 0.36 (toluene/ethyl acetate: 2/1),

Workup

  1. stirringthe mixture was stirred at room temperature until all the starting material
  2. customhad reacted (about 1 hour, thin layer chromatography check)
  3. extractionextracted five times with 600 ml of diethyl ether each time
  4. dry with materialDrying of the organic extracts (MgSO4)

Sources & evidence

ORD record
ord-4c4ad47c262b4c2096004c53a5010bd9
Source dataset
uspto-grants-1988_06
Patent number
US04751315

Reaction notes

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