Carbonate Ion → 3-[2-(trifluoromethyl)-4'-(methylthio)benzhydryloxy]-N-(1-adamantyl)azetidine-1-carboxamide

To a solution of 3-[2-(trifluoromethyl)-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) (100 mg, 0.26 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.10 mmol/g; 250 mg, 0.84 mmol) and 1-adamantyl isocyanate (47 mg, 0.26 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which time it was poured onto a DCM-wetted SCX-2 (1 g) cartridge. The sample was eluted with DCM (18 mL), then evaporated to afford the desired product as a white, crystalline solid (70 mg, 51%).