Dimethylformamide → HCID 22320776, compound

HRID 1936621Notes

Reaction equation

HRID 1936621 reaction equation
CN(C)C=O.[C:6]([O:10][C:11]([C@H:13]1[CH2:15][C@H:14]1[CH:16]1[CH2:20][CH2:19][NH:18][C:17]1=[O:21])=[O:12])([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([N:18]1[CH2:19][CH2:20][CH:16]([CH:14]2[CH2:15][CH:13]2[C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12])[C:17]1=[O:21])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 54047554HCID 54047554, compound

Product 1

HCID 22320776HCID 22320776, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of a dimethylformamide solution of 2.288 g (10.2 mmol) of 3-(cis-2-t-butoxycarbonylcyclopropyl)pyrrolidin-2-one was added 406.2 mg (10.2 mmol) of sodium hydride under cooling with ice, followed by stirring at room temperature for 1.5 hours. Then, 1.81 ml (15.3 mmol) of benzyl chloride was added thereto dropwise, followed by stirring for 2.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and the organic layer was washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to give 1.121 g (35.0%) of 1-benzyl-3-(2-t-butoxycarbonylcyclopropyl)pyrrolidin-2-one (isomer A: an isomer attributed to the steric configuration of the cyclopropyl group bonded to the carbon atom of the pyrrolidine ring) as a colorless solid. The column was then eluted with hexane:ethyl acetate=1:1 to give 670.9 mg (20.9%) of 1-benzyl-3-(cis-2-t-butoxycarbonylcyclopropyl)pyrrolidin-2-one (isomer B: an isomer attributed to the steric configuration of the cyclopropyl group bonded to the carbon atom of the pyrrolidine ring) as a colorless solid.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring for 2.5 hours
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed by evaporation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-c1c826b52c984699afb06e5df6842f46
Source dataset
uspto-grants-2002_05
Patent number
US06391889B1

Reaction notes

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