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

HRID 366876Notes

Reaction equation

HRID 366876 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.ClC1C=CC(S(O)(=O)=[O:21])=CC=1.O.C1C=C(Cl)C=C(C(OO)=O)C=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]2[O:21][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7400p-Chlorobenzenesulfonic acidHCID 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexaneYield 95.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 46.2 g (0.24 mol) of p-chlorobenzenesulfonic acid (produced by Tokyo Chemical Industry Co., Ltd.), 15.0 g of water, and 60.0 g of acetone in a round flask reactor, 31.1 g (0.13 mol) of 70% m-CPBA (m-chloroperbenzoic acid produced by Tokyo Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 10 hours at room temperature without irradiation by lamps. 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, 16.8 g of 1-benzyl-3,4-epoxypyrrolidine (yield 95.9%) was obtained.

Workup

  1. customto react for 10 hours at room temperature without irradiation by lamps
  2. customAfter completion, acetone was evaporated under reduced pressure
  3. extractionextracted with toluene and water
  4. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b4ce81bd097a467e87fb3c4ad0e3d6bc
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Reaction notes

Loading…