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

HRID 877709Notes

Reaction equation

HRID 877709 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.ClC1C=C(C=CC=1)C(OO)=[O:21]>C(Cl)Cl>[CH:3]12[O:21][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 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (24.00 g, 118 mmol) was dissolved in DCM (200 mL). Nitrogen was bubbled through it for ten minutes. Cooled to ˜0 degrees Celsius and added 3-chlorobenzoperoxoic acid (33.1 g, 148 mmol) in small portions with stirring. Let the suspension to stir overnight without removing the cold bath. The suspension was removed by filtration and the organic layer was washed with sat'd NaHCO3. The DCM soln. was dried (Na2SO4) and concentrated to give benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (22.5 g, 103 mmol, 87% yield). LCMS:M+23=242. Rt=1.57 min.

Workup

  1. customNitrogen was bubbled through it for ten minutes
  2. temperatureCooled to ˜0 degrees Celsius
  3. stirringto stir overnight
  4. customwithout removing the cold bath
  5. customThe suspension was removed by filtration
  6. washthe organic layer was washed with sat'd NaHCO3
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-91d04e9d76404fafa31a58a0652d6b21
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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