Sodium Hydroxide → 1-Boc-3-hydroxypiperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxypiperidine hydrochloride (827 mg, 6 mmol) in dioxane (12 ml) and water (6 ml) cooled to 0° C. is added 1 N NaOH (12 ml, 12 mmol) and dit-butyl carbonate (827 mg, 6 mmol) in dioxane (35 ml) and the reaction mixture is stirred at 25° C. for 1 hr. The reaction mixture is diluted with ethyl acetate, washed with aqueous sodium bicarbonate, 1 N KHSO4, water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 50% ethyl acetate in hexane) to give N-t-butoxycarbonyl-3-hydroxypiperidine (1.07 g).

Provenance & Evidence