Benzyl Bromide → HCID 22100535, compound

HRID 1457988Notes

Reaction equation

HRID 1457988 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH2:14]2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([N:16]1[CH2:17][CH:13]([C:9]2([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12][CH2:11][CH2:10]2)[CH2:14][C:15]1=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 11777088HCID 11777088, compound

Product 1

HCID 22100535HCID 22100535, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 15.13 g (59.5 mmol) portion of 4-(1-tert-butoxycarbonylaminocyclobutyl)-2-pyrrolidone was dissolved in 30.0 ml of N,N-dimethylformamide, cooled in an ice bath, mixed with 2.62 g (65.44 mmol) of sodium hydride (60% oil suspension) and then stirred at room temperature for 30 minutes. This was mixed with 7.78 ml (65.44 mmol) of benzyl bromide and stirred overnight at room temperature. Since the starting material partially remained, 1.19 g (29.74 mmol) of sodium hydride and 3.54 ml (29.74 mmol) of benzyl bromide were further added and stirred for additional 5 hours at room temperature. After evaporation of the solvent, the resulting residue was mixed with water, extracted with ethyl acetate and washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated. Thereafter, the resulting residue was purified by a silica gel column chromatography (silica gel 800 ml, ethyl acetate:hexane=10:1→1:1→2:1) to yield 5.65 g (28%) of the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred overnight at room temperature
  3. stirringstirred for additional 5 hours at room temperature
  4. customAfter evaporation of the solvent
  5. additionthe resulting residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. washwashed with saturated brine
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. customThereafter, the resulting residue was purified by a silica gel column chromatography (silica gel 800 ml, ethyl acetate:hexane=10:1→1:1→2:1)

Sources & evidence

ORD record
ord-17941444f7864256bcfd4c80cc88c4eb
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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