反应详情

To 4-fluoro-1-nitro-2-(trifluoromethyl)benzene (8) dissolved in 3 vol DCM, tetrabutylammoniumbromide (0.05 eq) and 50 wt % KOH (3.6 eq) were added. 7-azabicyclo[2.2.1]heptane hydrochloride (9) was then added at 0-5° C. The reaction was warmed to ambient temperature. The reaction was monitored by HPLC, and when the substrate was <1% AUC, the reaction was considered complete, and the layers are separated. The organic layer was washed with 1M HCl, and the aqueous layer was discarded. The organic layer was then washed once with water, once with brine, and evaporated. The resulting material was recrystallized from cyclohexane at reflux. The solid was filtered, washed with cyclohexane, and dried in a vacuum oven at 45° C. under a nitrogen atmosphere to provide 7-[4-nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane.

1. additionwere added
2. customthe layers are separated
3. washThe organic layer was washed with 1M HCl
4. washThe organic layer was then washed once with water, once with brine
5. customevaporated
6. customThe resulting material was recrystallized from cyclohexane
7. temperatureat reflux
8. filtrationThe solid was filtered
9. washwashed with cyclohexane
10. customdried in a vacuum oven at 45° C. under a nitrogen atmosphere