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

HRID 366874Notes

Reaction equation

HRID 366874 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.C1C=C(Cl)C=C(C(OO)=O)C=1>CO>[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

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 70297m-Chloroperbenzoic acidHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexaneYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 methanol 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, methanol was evaporated under reduced pressure, neutralized by NaOH (aq), and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 16.9 g of 1-benzyl-3,4-epoxypyrrolidine (yield 96.7%) was obtained.

Workup

  1. customto react for 10 hours at room temperature without irradiation by lamps
  2. customAfter completion, methanol 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-8cc210cb9e0c481e89771ac1b719a460
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Reaction notes

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