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

HRID 928189Notes

Reaction equation

HRID 928189 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 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2,5-dihydro-1H-pyrrole-1-carboxylate (130 g, 0.77 mol) in CH2Cl2 (0.8 L) was added mCPBA (233 g, 1.15 mol) portion wise at 5° C. After addition, the resulting mixture was warmed to rt and stirred overnight. The resulting solid was filtered off and the filtrate was washed with sat. aq. Na2SO3 to pH=7-8, then washed with sat. aq. NaHCO3 (3×200 mL) and brine (0.2 L). The organic layer was concentrated and the residue was distilled under reduced pressure to give the title compound (110 g, 77% yield) as a light yellow liquid. Used as is in the next step.

Workup

  1. additionAfter addition
  2. filtrationThe resulting solid was filtered off
  3. washthe filtrate was washed with sat. aq. Na2SO3 to pH=7-8
  4. washwashed with sat. aq. NaHCO3 (3×200 mL) and brine (0.2 L)
  5. concentrationThe organic layer was concentrated
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e9cab79ebea04a4e8058256b16c173b5
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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