m-Chloroperbenzoic acid → Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 1814036Notes

Reaction equation

HRID 1814036 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]2[CH:13]([O:21]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl-3-pyrroline-1-carboxylate (5 g, 24.6 mmol) and 3-chloroperoxybenzoic acid (8.5 g, 49.2 mmol) were dissolved in dichloromethane (250 μL) and stirred for 16 h at room temperature. The reaction mixture was washed with sat. NaHCO3, brine and dried (MgSO4). The title compound was isolated by silica gel chromatography (0-35% EtOAc-hexanes).

Workup

  1. washThe reaction mixture was washed with sat. NaHCO3, brine
  2. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-fcbfb9cacdb14bab9ba4210e4d15dfae
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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