C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][C@H:9]1[CH2:21][OH:22])=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][C@H:9]1[CH2:21][OH:22](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.
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