Dabco → 1-(2-(Tert-butoxycarbonylamino)ethyl)-4-aza-1-azonia-bicyclo[2.2.2]octane bromide

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To a solution of 1,4-diazabicyclo[2.2.2]octane (0.40 g, 3.57 mmol) in ether (5 mL) was added tert-butyl 2-bromoethylcarbamate (0.80 g, 3.57 mmol). The reaction was stirred overnight and the solvent was removed in vacuo. EtOAc (10 mL) was added and the reaction was stirred vigorously overnight. The precipitates were collected by filtration to give 1-(2-(tert-butoxycarbonylamino)ethyl)-4-aza-1-azonia-bicyclo[2.2.2]octane bromide (0.84 g) as a white solid. The solids were dissolved in MeOH (3 mL) and 4 M HCl in dioxane (3.5 mL, 14 mmol). The reaction was stirred at room temperature until it was determined to be complete by LCMS. The mixture was filtered to afford 1-(2-aminoethyl)-4-aza-1-azoniabicyclo[2.2.2]octane chloride hydrochloride (0.74 g) as a white solid. 1H-NMR (D2O, 400 MHz) δ 3.98-3.72 (m, 8H), 3.79-3.69 (m, 6H), 3.66-3.61 (m, 2H).

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