Sodium Hydroxide → 1-Boc-3-hydroxypiperidine

HRID 2185960Notes

Reaction equation

Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[OH-].[Na+].[C:11](=O)([O:17]C(C)(C)C)[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]>O1CCOCC1.O.C(OCC)(=O)C>[C:13]([O:12][C:11]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([OH:2])[CH2:4]1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 25 °C

Procedure

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).

Workup

washwashed with aqueous sodium bicarbonate, 1 N KHSO4, water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude product is purified by flash chromatography (silica gel, 50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-cf83874f538d4291a0ab80bf0acd3bc0
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403612B2

Reaction notes

Loading…