Sodium Acetate → (3E)-1-benzyl-3-methoxyimino-5,5-dimethylpyrrolidin-2-one

HRID 1366615Notes

Reaction equation

HRID 1366615 reaction equation
[CH3:1][C:2]1([CH3:16])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5](=[O:14])[C:4](=O)[CH2:3]1.C([O-])(=O)C.[Na+].Cl.[CH3:23][O:24][NH2:25]>CO>[CH3:23][O:24]/[N:25]=[C:4]1/[C:5](=[O:14])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]([CH3:16])([CH3:1])[CH2:3]/1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 669359741-Benzyl-5,5-dimethylpyrrolidine-2,3-dione

Product 1

HCID 87210255(3E)-1-benzyl-3-methoxyimino-5,5-dimethylpyrrolidin-2-oneYield 102.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione (3.9036 g, 17.97 mmol) in MeOH (90 mL) was added sodium acetate (1.81 g, 21.54 mmol) and methoxyamine hydrochloride (1.80 g, 21.55 mmol). The solution was stirred overnight and the solvent was then removed in vacuo. The residue was partitioned between DCM (200 mL), sat. aq. NaHCO3, and water. The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to provide crude (3E)-5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione 3-(O-methyloxime) (4.5282 g, >100% crude yield) as a yellow/orange oil. LCMS: (M+H)+: 247.1.

Workup

  1. customthe solvent was then removed in vacuo
  2. customThe residue was partitioned between DCM (200 mL), sat. aq. NaHCO3, and water
  3. extractionThe aqueous phase was extracted with a fresh portion of DCM (50 mL)
  4. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70e26ca5a25542a39aed0f086cce7492
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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