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

HRID 473560Notes

Reaction equation

HRID 473560 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>[C:9]([O:8][C:6]([N:1]1[CH2:5][CH:4]2[CH:3]([O:21]2)[CH2:2]1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

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 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2,5-dihydro-1H-pyrrole-1-carboxylate (10 g, 0.059 mol) in DCM (200 mL) was added MCPBA (14.5 g, 0.065 mol) and the mixture stirred for 18 h. After this time the mixture was washed with water (50 mL) and sodium bicarbonate solution (50 mL), dried (Na2SO4), filtered and the volatiles evaporated in vacuo. The crude product was purified by chromatography (SiO2; 10% ethyl acetate in DCM), yielding the title compound as a colourless oil (6.2 g, 59%). δH (DMSO-d6) 3.74 (2H, m), 3.57 (2H, m), 3.25 (2H, m), 1.38 (9H, s).

Workup

  1. washAfter this time the mixture was washed with water (50 mL) and sodium bicarbonate solution (50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe volatiles evaporated in vacuo
  5. customThe crude product was purified by chromatography (SiO2; 10% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-57a7d6f9bd374680a179fd20fe907a78
Source dataset
uspto-grants-2014_01
Patent number
US08637491B2

Reaction notes

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