1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

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Reaction Steps

To a stirred solution of 1-tert-butyl 4-ethyl 1,4-piperidinedicarboxylate (Preparation 49, 12.8 g, 0.05 mol) in benzene (300 ml) under nitrogen was added slowly diisobutyl aluminium hydride (1 M solution, 100 ml, 0.1 mol). The reaction mixture was stirred at room temperature for 3 h before quenching by the addition of water (100 ml) followed by addition of hydrochloric acid (1 M) to adjust to pH 4. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated to give an oil. The crude oil was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (6:4) to give the title compound as an oil (5.0 g, 46%).

Provenance & Evidence