Water → 3-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

HRID 1018055Notes

Reaction equation

HRID 1018055 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:14].O>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]2[O:14][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexaneYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, 15.0 g of water, and 60.0 g of acetone in a Pyrex round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 10 hours at room temperature with irradiation by 500W Xe lamps (UXL-500D xenon lamp produced by Ushio). After completion, acetone was evaporated under reduced pressure, neutralized by NaOH (aq), and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 4.9 g of 1-benzyl-3,4-epoxypyrrolidine (yield 28.0%) was obtained and 11.9 g (yield 75.0%) of 1-benzyl-3-pyrroline was recovered.

Workup

  1. customAfter completion, acetone was evaporated under reduced pressure
  2. extractionextracted with toluene and water
  3. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7c064abf765145cabfa1004b72022cf9
Source dataset
uspto-grants-2002_11
Patent number
US06479668B1

Reaction notes

Loading…