Aluminium lithium hydride → 1,1-Dimethylethyl 4-(2-hydroxy-1,1-dimethylethyl)-1-piperazinecarboxylate

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Reaction Steps

To a solution of 4-(1-ethoxycarbonyl-1-methylethyl)piperazine-1-carboxylic acid tert-butyl ester (500 mg, 1.67 mmol) in THF (5 mL) at 0° C. was added LiAlH4 (3 mL, 1M in THF) drop wise. The resulting mixture was allowed to stir for 2.5 h then quenched with H2O (0.1 mL), 20% aq. NaOH (0.1 mL) and H2O (0.3 mL). The mixture was diluted with EtOAc and H2O, filtered through Celite® then the organic layer separated, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as a colourless oil (217 mg, 50%). 1H NMR (CDCl3, 400 MHz): δ 5.30 (1 H, brd s), 3.42 (6 H, m), 3.35 (4 H, brd s), 2.51 (6 H, brd s), 1.03 (9 H, s)

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