Piperidin-2-ylmethanol → [1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-yl]-methanol

HRID 1643457

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([O:13]C2C(F)=C(F)C(F)=C(F)C=2F)(=[O:12])=O)=[C:5]([CH3:25])[CH:4]=1.[OH:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:25])[C:6]([S:10]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH:28]2[CH2:27][OH:26])(=[O:12])=[O:13])=[C:7]([CH3:9])[CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

Perfluorophenyl 4-methoxy-2,6-dimethylbenzenesulfonate (1 g, 2.616 mmol), 2-(hydroxymethyl)-piperidine (1.61 g, 13.079 mmol) and tetrabutylammonium chloride (1.45 g, 5.231 mmol) were dissolved in N,N-dimethylformamide (10 ml) and the solution was stirred at 110° C. for 1 h. The solvent was removed in vacuo, the residue was dissolved in ethyl acetate and the solution was washed with ammonium chloride solution (10%, 20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with diethyl ether/hexane/methylene chloride (1:1:1). Yield: 0.63 g (76%)

Aufarbeitung

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in ethyl acetate
washthe solution was washed with ammonium chloride solution (10%, 20 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography (silica gel) with diethyl ether/hexane/methylene chloride (1:1:1)

Quellen und Nachweise

ORD-Eintrag: ord-f06854afd3cf4fe5846e8e0bf8757fd8
Quelldatensatz: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08119805B2

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