2-Bromoethanol → [1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

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Reaction Steps

2-Bromo-ethanol (2.38 mL, 33.5 mmol, 1.0 eq) is added at room temperature to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (7.0 g, 33.5 mmol, 1.0 eq) in N,N-dimethylformamide (300 mL), followed by potassium carbonate (4.64 g, 33.5 mmol, 1.0 eq). After 6 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×40 mL) and water (40 mL). pH of the aqueous layer is neutralized with a 0.1 N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford [1-(2-hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as an off-white oil (7.96 g, 97% yield).

Provenance & Evidence