Benzyl Bromide → 1-Benzyl-5-butoxypyrrolidin-2-one

HRID 1639038Notes

Reaction equation

HRID 1639038 reaction equation
[CH2:1]([O:5][CH:6]1[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH3:4].[OH-].[K+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH2:14]([N:10]1[CH:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH2:7][CH2:8][C:9]1=[O:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 15696557HCID 15696557, compound

Product 1

HCID 30779611-Benzyl-5-butoxypyrrolidin-2-oneYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4 g of 5-n-butyloxy-pyrrolidin-2-one, 1.79 g of potassium hydroxide hydrated to 85%, and 0.4 g of n-tetrabutylammonium bromide in 80 cm' of tetrahydrofuran, there is added a solution of 4.35 g of benzyl bromide, without exceeding 30° C. After agitating for 1 hour at ambient temperature, the insoluble matter is filtered off and the solvent is evaporated. The residue (4.7 g) is distilled at 230° C. under 0.05 mbar, then the distillate is chromatographed on silica (eluent: ethyl acetate--n-hexane, 1--1). 3.5 g of the expected product is obtained.

Workup

  1. customwithout exceeding 30° C
  2. filtrationthe insoluble matter is filtered off
  3. customthe solvent is evaporated
  4. distillationThe residue (4.7 g) is distilled at 230° C. under 0.05 mbar
  5. distillationthe distillate is chromatographed on silica (eluent: ethyl acetate--n-hexane, 1--1)

Sources & evidence

ORD record
ord-5a0ef2c087df4ed9b59733745d74071d
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

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