反应详情

4-fluoro-1-nitro-2-(trifluoromethyl)benzene was dissolved in 3 vol DCM. Tetrabutylammoniumbromide (0.05 eq) and KOH (50 wt %, 3.6 eq) were added. 7-azabicyclo[2.2.1]heptane hydrochloride (8-HCl) was then added at 0-5° C. The reaction was warmed up to ambient temperature and monitored by HPLC. Once substantially complete, the layers were separated and the organic layer was washed with 1M HCl. The layers were separated and the aqueous layer was discarded. The organic layer was washed once with water, once with brine, and then distilled. 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. with a N2 gas bleed to provide 7-[4-nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane (9).

1. customOnce substantially complete, the layers were separated
2. washthe organic layer was washed with 1M HCl
3. customThe layers were separated
4. washThe organic layer was washed once with water, once with brine
5. distillationdistilled
6. customThe resulting material was recrystallized from cyclohexane
7. temperatureat reflux
8. filtrationThe solid was filtered
9. washwashed with cyclohexane
10. dry with materialdried in a vacuum oven at 45° C. with a N2 gas