Dimethyl Sulfoxide → Benzyl 4-(2-azido-3,3,3-trifluoropropoxy)piperidine-1-carboxylate
Reaktionsgleichung
[F:1][C:2]([F:28])([F:27])[CH:3](OS(C)(=O)=O)[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1.[N-:29]=[N+:30]=[N-:31].[Na+].CS(C)=O>O>[N:29]([CH:3]([C:2]([F:28])([F:27])[F:1])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)=[N+:30]=[N-:31]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of benzyl 4-{3,3,3-trifluoro-2-[(methylsulfonyl)oxy]propoxy}piperidine-1-carboxylate (1.31 g), sodium azide (1.00 g), 15-crown-5-ether (3.39 g) and dimethyl sulfoxide (5 mL) was stirred at 100° C. for 3 days. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (294 mg).
Aufarbeitung
- extractionthe obtained mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-2be79847caf444ccb0b82b8f22b1b84a
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- US08703758B2
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