m-Chloroperbenzoic acid → Naphthalen-2-ylmethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
Reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N:12]1([C:18]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)=[O:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]1>C(Cl)Cl>[CH:14]12[O:9][CH:15]1[CH2:16][CH2:17][N:12]([C:18]([O:20][CH2:21][C:22]1[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=1)=[O:19])[CH2:13]2Participants
4
Procedure
A suspension of mCPBA (13.02 g, 58.13 mmol) dissolved in methylene chloride (50 mL) was added dropwise to a cooled (0° C.) solution of naphthalen-2-ylmethyl 5,6-dihydropyridine-1(2H)-carboxylate (11 g, 41.5 mmol) dissolved in methylene chloride (33 mL). The solution was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched with 5% K2CO3 and then the layers were separated. The organic phase was washed with 5% K2CO3, saturated NaCl, dried over Na2SO4and concentrated in vacuo (9.5 g).