GENERAL STEPS: 4-Aminotetrahydro-2H-pyran-4-carbonitrile (10 g, 80 mmol) was slowly added to a suspension of LiAlH4 (9.1 g, 240 mmol) in methyl tertiary butyl ether (MTBE, 120 mL) at room temperature. The reaction mixture was stirred continuously at 40 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by sequential addition of water (9.1 mL) and 15% aqueous NaOH solution (9.1 mL), followed by water (27.3 mL). After continued stirring for 1 h, the reaction mixture was filtered and the filter cake was washed with MTBE (20 mL x 2). After combining the filtrates, 4-(aminomethyl)tetrahydro-2H-pyran-4-amine (6 g, 46.1 mmol) was obtained by vacuum concentration, and the product could be used in subsequent reactions without further purification.
