O-methylhydroxylammonium chloride → benzyl (4Z)-4-methoxyimino-3,3-dimethylpyrrolidine-1-carboxylate

HRID 877706Notes

Reaction equation

HRID 877706 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+].[CH3:24][O:25][NH3+:26].[Cl-]>CO>[CH3:24][O:25]/[N:26]=[C:6]1/[C:2]([CH3:18])([CH3:1])[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]/1

Participants

5

Reactant 3

HCID 11639O-methylhydroxylammonium chlorideHCID 517045Sodium AcetateHCID 66936222Benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate

Product 1

HCID 87210112benzyl (4Z)-4-methoxyimino-3,3-dimethylpyrrolidine-1-carboxylateYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl 3,3-dimethyl-4-oxopyrrolidine-1-carboxylate (2.91 g, 11.8 mmol) in MeOH (10 mL) was added sodium acetate (1.93 g, 23.5 mmol) and o-methylhydroxylamine hydrochloride (1.97 g, 23.5 mmol). The mixture was stirred at rt for 18 h. The reaction was concentrated and then diluted with dichloromethane (200 mL). The organic layer was washed with water (20 mL) and aq. sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated. (Z)-benzyl 4-(methoxyimino)-3,3-dimethylpyrrolidine-1-carboxylate (3.17 g, 97% yield) was obtained as a colorless oil. m/z: 277.17 (M+H); LC retention time: 2.83 min (analytical HPLC Method I).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with dichloromethane (200 mL)
  3. washThe organic layer was washed with water (20 mL) and aq. sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-72c5198119874aa4ae1e7401472eabce
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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