1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

HRID 379933

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([O-:22])(=[S:21])[CH3:20].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:19]([S:21][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)(=[O:22])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

In 40 ml of dimethylformamide were dissolved 4.12 g (14.7 mmol) of 1-(tert-butoxycarbonyl)-4-(methanesulfonyloxy)piperidine, and 2.53 g (2.21 mmol) of potassium thioacetate were added to the solution, followed by stirring of the resulting mixture at 105° C. for 4 hours under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water and then a saturated aqueous NaCl solution, followed by evaporation of the solvent. The thus obtained residue was subjected to silica gel column chromatography and the fractions eluted with a mixed solvent of hexane-ethyl acetate (5:1) were collected to obtain 5.19 g (yield: 81%) of the title compound as an oil.

Aufarbeitung

additionwere added to the solution
temperatureAfter cooling
washwashed with water
customa saturated aqueous NaCl solution, followed by evaporation of the solvent
washthe fractions eluted with a mixed solvent of hexane-ethyl acetate (5:1)
customwere collected

Quellen und Nachweise

ORD-Eintrag: ord-bffff60e8d2d40cca11441a4679f6732
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06300357B1

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