m-Chloroperbenzoic acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 1972088Notes

Reaction equation

HRID 1972088 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]2[CH:12]([O:22]2)[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (19.1 mmol, 3.5 g), in DCM (50 mL) cooled at 0° C., was added m-CPBA (32.2 mmol, 5.95 g (70%)) portion wise. The reaction was stirred at room temperature for 4 h. The reaction was diluted with DCM (50 mL) and washed with sat. Na2S2O3, sat. NaHCO3, water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on a SiO2 cartridge (5% EtOAc in hexane -25% EtOAc in hexane) to provide 7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester.

Workup

  1. washwashed with sat. Na2S2O3, sat. NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on a SiO2 cartridge (5% EtOAc in hexane -25% EtOAc in hexane)

Sources & evidence

ORD record
ord-b57bbcabd1a747d8abb5d83287c6da7a
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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