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

HRID 1015984Notes

Reaction equation

HRID 1015984 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 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30 g (133 mmol) of benzyl 3-pyrroline-1-carboxylate in 700 mL of methylene chloride was added 57.2 g (200 mmol) of mCPBA. The reaction mixture was stirred at room temperature overnight and quenched with 250 mL of 20% NaHSO3 aqueous solution. The organic phase was separated, and the aqueous layer was extracted with methylene chloride twice (100 mL×2). The combined extracts were washed with saturated NaHCO3 aqueous solution twice (250 mL×2), brine, dried over Na2SO4, evaporated under reduced pressure. Chromatography on silica gel column with 40% EtOAc-Hexane provided the title compound (24 g, 83%). MS (M+H)+ 220.

Workup

  1. customquenched with 250 mL of 20% NaHSO3 aqueous solution
  2. customThe organic phase was separated
  3. extractionthe aqueous layer was extracted with methylene chloride twice (100 mL×2)
  4. washThe combined extracts were washed with saturated NaHCO3 aqueous solution twice (250 mL×2), brine
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2586ca0cb35e427ea605b229514a0f47
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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