(+-)-3-Quinuclidinol → N-(4-Bromophenyl)carbamic Acid 1-azabicyclo[2.2.2]octan-3-yl Ester
Reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:18](=[O:19])[NH:17][C:14]1[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=1)[CH2:2]2Participants
3
Procedure
3-Quinuclidinol and 4-bromophenyl isocyanate were used. Filtration of the precipitated solid from the cooled reaction mixture afforded the title compound (60%) as a white solid: mp 217.5-219.5° C.; FAB LRMS m /z (relative intensity, %) 328 (16), 327 ([MH+ with Br81 ], 100), 326 (16), 325 ([MH+ with Br79 ], 100).
Workup
- filtrationFiltration of the precipitated solid
- customfrom the cooled reaction mixture