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

HRID 1018058Notes

Reaction equation

HRID 1018058 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 94.7%

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 quartz 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 5 days 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), extracted with toluene and water. After the solvent was evaporated under reduced pressure, 16.6 g of 1-benzyl-3,4-epoxypyrrolidine (yield 94.7%) was obtained and 1-benzyl-3-pyrroline was not 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-cad7b87ad9824ab4908d6215f99c0918
Source dataset
uspto-grants-2002_11
Patent number
US06479668B1

Reaction notes

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