Benzene, 1-bromo-3-(trifluoromethyl)- → Tert-butyl 5-[3-(trifluoromethyl)phenyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

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A 50 ml round bottom equipped with stir bar was charged with binap (0.146 g, 0.23 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.088 g, 0.10 mmol) dissolved in dioxane (5 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 1-bromo-3-(trifluoromethyl)benzene (0.323 g, 1.44 mmol) followed by tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.2 g, 0.96 mmol) and SODIUM TERT-BUTOXIDE (0.380 g, 3.83 mmol) were added, and the reaction was stirred at 80 °C for 2 hrs. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous phase was extracted with EtOAc (3X20mL), combined, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was loaded on a Snap KP-SIL 25g column and purified on a Biotage SP4 instrument, eluting with 10% to 35% ethyl acetate in heptane to provide tert-butyl 5-(3-(trifluoromethyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.305 g, 93 %) as an oil.

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