m-Chloroperbenzoic acid → 7-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid

HRID 1095177Notes

Reaction equation

HRID 1095177 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[CH:10]12[O:22][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([OH:5])=[O:7])[CH2:9]2

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 221275607-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (Aldrich, 15.99 g, 87.28 mmol) in methylene chloride (600 mL) at 0° C., mCPBA (Aldrich, 29.4 g, 77%, 131 mmol) was added and the mixture was stirred overnight. The reaction was quenched with 10% Na2S2O3 and the organic layer was separated and washed with 5% sodium carbonate, brine and water and dried over sodium sulfate and concentrated to give a light yellow oil, which was chromatographied (10% EtOAc/Hexane) to yield a colorless oil. 14.93 g. The compound was used directly for the next step.

Workup

  1. customThe reaction was quenched with 10% Na2S2O3
  2. customthe organic layer was separated
  3. washwashed with 5% sodium carbonate, brine and water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a light yellow oil, which
  7. customto yield a colorless oil

Sources & evidence

ORD record
ord-088a3f803da445b1b193ed513820141b
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

Loading…