O-Methylhydroxylamine hydrochloride → HCID 86604848, compound

HRID 2230244Notes

Reaction equation

HRID 2230244 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:23][O:24][NH2:25]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[N:25][O:24][CH3:23])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 150432781-Benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

Product 1

HCID 86604848HCID 86604848, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Benzyloxycarbonyl-4-ethoxycarbonyl-3-oxopyrrolidine (196.7 g, 600.0 mmol) was dissolved in pyridine (700 ml) and mixed with O-methylhydroxylamine hydrochloride (76.55 g, 916.5 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes and then at room temperature for 5 hours. Pyridine was evaporated under a reduced pressure, the residue was mixed with 1 N hydrochloric acid and ethyl acetate and then the mixture was shaken and subjected to separation of layers. The organic layer was washed with saturated brine, and the water layer was further extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and filtered, the solvent was evaporated under a reduced pressure and then the residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain 187.5 g (589.1 mmol, 98.2%) of the title compound.

Workup

  1. temperaturecooling
  2. waitat room temperature for 5 hours
  3. customPyridine was evaporated under a reduced pressure
  4. additionthe residue was mixed with 1 N hydrochloric acid and ethyl acetate
  5. stirringthe mixture was shaken
  6. customsubjected to separation of layers
  7. washThe organic layer was washed with saturated brine
  8. extractionthe water layer was further extracted with ethyl acetate
  9. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was evaporated under a reduced pressure
  12. customthe residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f793b987749143fc8ad935826fbe9424
Source dataset
uspto-grants-2002_07
Patent number
US06423843B1

Reaction notes

Loading…