Piperidin-4-ol → Tert-butyl 4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 25 g (247 mmol) 4-piperidinol in 350 mL dry tetrahydrofuran (THF) at 0° C. was added dropwise 60.2 g (276 mmol) di-t-butylcarbonate in 350 mL dry THF. The reaction was allowed to warm to room temperature (rt) and stirred overnight. The solvent was removed under reduced pressure, the resulting residue dissolved in 700 mL CH2Cl2 and the solution extracted with H2O (1×400 mL), dried over MgSO4, filtered and rotary evaporated to yield 45 g (91%) of N-(t-butoxycarbonyl)-4-piperidinol as an oil which slowly solidified to white crystals. 1H NMR (CDCl3) δ 3.75-3.96 (m, 3H); 2.92-3.13 (m, 2H); 1.80-1.93 (m, 4H); and 1.48 (s, 9H).

Provenance & Evidence