Sodium Acetate → benzyl (4Z)-4-methoxyimino-3,3-dimethylpyrrolidine-1-carboxylate

HRID 1366502Notes

Reaction equation

HRID 1366502 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6](=O)[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.C([O-])(=O)C.[Na+].Cl.[CH3:25][O:26][NH2:27]>CO>[CH3:1][C:2]1([CH3:18])[CH2:3][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]/[C:6]/1=[N:27]\[O:26][CH3:25]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 66936222Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate

Product 1

HCID 87210112benzyl (4Z)-4-methoxyimino-3,3-dimethylpyrrolidine-1-carboxylateYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl 3,3-dimethyl-4-oxo-1-pyrrolidinecarboxylate (0.9135 g, 3.694 mmol) in MeOH (37 mL) was added sodium acetate (0.606 g, 7.387 mmol) and O-methylhydroxylamine hydrochloride (0.620 g, 7.397 mmol). The solution was stirred for 3 h, and then concentrated in vacuo. The residue was partitioned between DCM (100 mL), water (5 mL), and sat. aq. NaHCO3 (30 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide phenylmethyl (4Z)-3,3-dimethyl-4-[(methyloxy)imino]-1-pyrrolidinecarboxylate (0.9124 g, 89% yield) as a pale yellow oil. LCMS: (M+H)+: 277.0.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between DCM (100 mL), water (5 mL), and sat. aq. NaHCO3 (30 mL)
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21a468e90f15483380a8e66ddca3629e
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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