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

HRID 2378340Notes

Reaction equation

HRID 2378340 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:13]S(O)(=O)=O.O.C1C=C(Cl)C=C(C(OO)=O)C=1>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]2[CH:10]([O:13]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 12153330HCID 12153330, compound

Product 1

HCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexaneYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To an ice-cooled solution of 1-benzyl pyrroline (0.01 mol), 98% H2SO4 (0.012 mol), water (1.5 g), and acetone (10 mL) in a round bottom flask was added 77% m-CPBA (0.013 mol) with stirring, and allowed to react for about 50 h at room temperature. After completion of the reaction (TLC monitor), acetone was evaporated under reduced pressure, and the mixture was neutralized by 1M NaOH, and extracted with toluene (30 mL×3). The precipitates that appeared were filtered, and the filtrate was repeatedly washed with water (30 mL×2). After the solvent was evaporated under reduced pressure, pure product was obtained in 77% yield via column chromatography (silica gel, CH2Cl2:EtOAc:MeOH, 7.5:2.00:0.5).

Workup

  1. customto react for about 50 h at room temperature
  2. customwas evaporated under reduced pressure
  3. extractionextracted with toluene (30 mL×3)
  4. customThe precipitates
  5. filtrationthat appeared were filtered
  6. washthe filtrate was repeatedly washed with water (30 mL×2)
  7. customAfter the solvent was evaporated under reduced pressure
  8. custompure product was obtained in 77% yield via column chromatography (silica gel, CH2Cl2:EtOAc:MeOH, 7.5:2.00:0.5)

Sources & evidence

ORD record
ord-bca5af43aaee4fbf8765cb0c1ee1a5ee
Source dataset
uspto-grants-2008_12
Patent number
US07470790B2

Reaction notes

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