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

반응식

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

참가 물질

실험 절차

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.