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

Participants

Reaction Steps

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.

Provenance & Evidence