m-Chloroperbenzoic acid → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 2400915Notes

Reaction equation

HRID 2400915 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:10]([O:21]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester (30 mmol) in DCM (50 mL) was added 40% MCPBA (1 equiv) and the resulting mixture was stirred at rt for 24 h. The solution was then extracted with aq. NaHCO3, dried (Na2SO4) and concentrated. Purification of the residue by silica gel chromatography (1-30% EtOAc in heptanes) afforded 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. extractionThe solution was then extracted with aq. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification of the residue by silica gel chromatography (1-30% EtOAc in heptanes)

Sources & evidence

ORD record
ord-b86d48d410f54e07a592059c5673b396
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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