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

HRID 639085Notes

Reaction equation

HRID 639085 reaction equation
[N:1]1([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH:3]12[O:21][CH:4]1[CH2:5][N:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2]2

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-carboxylateYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl 2,5-dihydro-1H-pyrrole-1-carboxylate (5.0 g, 29.55 mmole) in DCM (200 mL) at RT was added MCPBA (7.65 g, 44.3 mmole). After 24 h, the reaction contents were washed with 10% aqueous NaHCO3 and dried over Na2SO4. Purification on silica (hexanes/EtOAc, 1:1) afforded the title compound (4.5 g, 82%) as a yellow oil: LC-MS (ES) m/e 186 (M+H)+.

Workup

  1. customthe reaction contents
  2. washwere washed with 10% aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. customPurification on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-cefbe61c2a5f4af89c47e09c3a62985d
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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