Aluminium lithium hydride → (S)-(1,4-Dimethylpiperazin-2-YL)methanol

(S)-2-hydroxymethyl-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (5.66 g, 17.9 mmol) was dissolved in THF (10 mL) and cooled to 0° C. 2M LiAlH4 in THF (28.5 mL, 57.0 mmol) was added. The reaction mixture was stirred at reflux for 4 hours and then cooled to 0° C. and quenched with the drop-wise addition of 1M sodium hydroxide solution (20 mL). The reaction mixture was diluted with THF (50 mL), filtered and the filtrate was concentrated in vacuo to give 1,4-dimethyl-(S)-2-hydroxymethyl piperazine (1.44 g, 56%) as a colourless oil which was used without further purification.