Methyl iodide → HCID 56970590, compound

HRID 639104Notes

Reaction equation

HRID 639104 reaction equation
[C:1]([CH:3]1[C:7](=[O:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].[C:16]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[C:1]([C:3]1([CH3:16])[C:7](=[O:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2756790tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

Product 1

HCID 56970590HCID 56970590, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-cyano-4-oxo-1-pyrrolidinecarboxylate (3.9 g, 18.6 mmol) in acetone (185 mL) were added K2CO3 (3.07 g, 22.3 mmol) and MeI (1.39 mL, 22.3 mmol). After 12 h at reflux, the solution was cooled and the solid precipitate filtered. The filtrate was then concentrated and the residue purified by column chromatography (silica, 0.5% MeOH in DCM (1% NH4OH)) affording the title compound (2.3 g, 55%) as a yellow oil: LCMS (ES) m/e 225 (M+H)+.

Workup

  1. temperatureAfter 12 h at reflux
  2. temperaturethe solution was cooled
  3. filtrationthe solid precipitate filtered
  4. concentrationThe filtrate was then concentrated
  5. customthe residue purified by column chromatography (silica, 0.5% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-62e9588247544425984a50e68954d40b
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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