Methanesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 1530559Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (4.50 g, 22.4 mmol, 1.0 eq) and TEA (11.3 g, 5.0 eq) in DCM (30.0 mL) at 0° C. was added MsCl (5.10 g, 44.5 mmol, 2.0 eq) in DCM (10.0 mL) dropwise. The resulting mixture was stirred at 0° C. for 30 min and then warmed to room temperature with stirring for 3 hr. After being quenched with water and extracted with ethyl acetate, the organic layers were combined, washed with brine, dried over MgSO4, filtered, and evaporated to afford the crude product, which was purified via silica gel chromatography eluting with EtOAc/petroleum ether (1:5) to afford tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (4.8 g, 77% yield) as pale yellow solid. LCMS (ESI) m/z: 224.1 [M-56+H+].

Workup

temperaturewarmed to room temperature
stirringwith stirring for 3 hr
customAfter being quenched with water
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customto afford the crude product, which
customwas purified via silica gel chromatography
washeluting with EtOAc/petroleum ether (1:5)

Sources & evidence

ORD record: ord-86783ba3be1b4051b8ff9296ce58689f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

Loading…