Methyl iodide → 1-Benzyl 3-ethyl 3-methyl-4-oxopyrrolidine-1,3-dicarboxylate

HRID 353593Notes

Reaction equation

HRID 353593 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:22])[C:13](=[O:21])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 150432781-Benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

Product 1

HCID 572801371-Benzyl 3-ethyl 3-methyl-4-oxopyrrolidine-1,3-dicarboxylateYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of N-benzyloxycarbonyl-4-ethoxycarbonylpyrrolidin-3-one (291 g) in acetone (1.5 l) was added potassium carbonate (200 g), followed by iodomethane (300 mL), and then the solution was refluxed for 3 hr. The reaction mixture was cooled at room temperature, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:6) to obtain the desired compound, (237.7 g, 80.7%).

Workup

  1. temperaturethe solution was refluxed for 3 hr
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:6)

Sources & evidence

ORD record
ord-fb997c39a0714c19ac01c73f5f991ff1
Source dataset
uspto-grants-2004_06
Patent number
US06753430B2

Reaction notes

Loading…