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

HRID 1366479Notes

Reaction equation

HRID 1366479 reaction equation
[N:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH:3]12[O:24][CH:4]1[CH2:5][N:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2]2

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-carboxylateYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of phenylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate (10.30 g, 50.68 mmol) in DCM (250 mL) was added m-CPBA (wet; ca. 75%; 17.49 g). The solution was stirred and warmed to room temperature overnight. The solution was diluted with DCM and washed with 2×10% aq. NaHCO3-1 N aq. NaOH (1:1). The organic phase was dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel chromatography (40% EtOAc in hexanes) to give phenylmethyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (7.90 g, 71% yield) as a light yellow oil.

Workup

  1. washwashed with 2×10% aq. NaHCO3-1 N aq. NaOH (1:1)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-145947ed8a724aa385ff52425c474114
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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