Triethylamine → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (5.0 g, 36 mmol) and triethyl amine (6.0 ml, 43 mmol) in 50 ml of THF at 0° C. under an atmosphere of nitrogen was added MsCl (3.4 ml, 43 mmol). The mixture was stirred at 0° C. for 3 h and quenched with aqueous sodium hydrogen carbonate (saturated, 100 mL). The mixture was extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with brine (1×100 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/isohexane to hexanes to afford the title compound as a colorless solid (4.2 g, 42%). 1H-NMR (500 MHz, CDCl3) δ 4.90 (s, 1H), 3.70 (m, 2H), 3.30 (m, 2H), 3.05 (s, 3H), 1.95 (m, 2H), 1.82 (m, 2H), 1.45 (s, 9H).

Provenance & Evidence