E) Synthesis of quinuclidinium-4-ylmethylamine
4-Cyanoquinuclidine (0.30 g, 2.2 mmol) was dissolved in ether (5 mL) and slowly added to an ether suspension of lithium aluminum hydride (LAH, 0.167 g, 4.41 mmol). The reaction system was cooled at 0 °C and additional ether (15 mL) was added. Subsequently, the reaction mixture was stirred at 23 °C for 3 hours. Upon completion of the reaction, the reaction was quenched with sodium sulfate decahydrate and stirring was continued for 30 minutes. Next, ethyl acetate was added and after 30 minutes, diatomaceous earth was added and the suspension was filtered through diatomaceous earth. The filtrate was concentrated to dryness to give the oily product quinuclidinium-4-ylmethylamine (0.310 g, quantitative yield). The product was used directly in the subsequent reaction without further purification.
1H NMR (400 MHz, CDCl3) δ ppm: 1.31-1.40 (6H, m), 2.43 (2H, s), 2.86-2.94 (6H, m).
