Sodium Acetate → HCID 87210078, compound

HRID 1366530Notes

Reaction equation

HRID 1366530 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6](=O)[CH2:5][CH2:4][N:3]1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].C([O-])(=O)C.[Na+].Cl.[CH3:23][O:24][NH2:25]>CO>[CH3:23][O:24]/[N:25]=[C:6]1/[C:2]([CH3:16])([CH3:1])[N:3]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:5]/1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 66936289HCID 66936289, compound

Product 1

HCID 87210078HCID 87210078, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-1-(phenylcarbonyl)-3-pyrrolidinone (2.0602 g, 9.482 mmol) in MeOH (50 mL) was added sodium acetate (0.956 g, 11.38 mmol) and methoxyamine hydrochloride (0.950 g, 11.37 mmol). The mixture was stirred overnight and then concentrated in vacuo. The residue was dissolved in DCM (200 mL) and washed with sat. aq. NaHCO3 (50 mL), water (50 mL), and brine (50 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford (3E)-2,2-dimethyl-1-(phenylcarbonyl)-3-pyrrolidinone O-methyloxime (1.9567 g, 84% yield) as a light yellow oil that solidified under high vacuum. LCMS: (M+H)+: 247.2.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM (200 mL)
  3. washwashed with sat. aq. NaHCO3 (50 mL), water (50 mL), and brine (50 mL)
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4602531715b7423ab1790d2e9f9b5246
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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