2,3-Dichloro-5-(trifluoromethyl)pyridine → Tert-butyl (1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)carbamate

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Reaktionsgleichung

Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][CH2:14]1.C(=O)([O-])N.[K+]>CN(C=O)C>[C:22]([O:21][C:20](=[O:26])[NH:19][CH:16]1[CH2:17][CH2:18][N:13]([C:2]2[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=2)[CH2:14][CH2:15]1)([CH3:25])([CH3:23])[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of 2,3-dichloro-5-(trifluoromethyl)pyridine (2.0 g, 9.26 mmol), tert-butyl piperidine-4-ylcarbamate (2.2 g, 11.11 mmol) and anhydrous potassium carbamate (3.8 g, 27.78 mmol) in DMF (15 ml) was heated in a microwave reactor at 150° C. for 10 min. The mixture was concentrated, water and EtOAc were added to the residue and the aqueous phase was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (hexane/EtOAc 90:10) to yield the title compound (2.5 g, 70%). 1H NMR (500 MHz, CDCl3): δ 1.47 s, 9H), 1.53-1.60 (m, 2H), 2.07-2.09 (m, 2H), 3.01-3.06 (m, 2H), 3.72 (br.s., 1H), 3.97-4.00 (m, 2H, 4.54 (br.s., 1H), 7.75 (s, 1H), 8.38 (s, 1H); Mass Spectrum: M+H+ 380.

Aufarbeitung

concentrationThe mixture was concentrated
additionwater and EtOAc were added to the residue
extractionthe aqueous phase was extracted with EtOAc
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated
customThe crude product was purified by flash column chromatography (hexane/EtOAc 90:10)

Quellen und Nachweise

ORD-Eintrag: ord-df58bb9f661042199d662b8efa6dd97a
Quelldatensatz: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07960380B2

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