Sodium Azide → (S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate
Reaktionsgleichung
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:20]([CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[N+:21]=[N-:22]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 10.50 g of {(3S)-1-(tert-butoxycarbonyl)-3-piperidyl}methyl methanesulfonate in 100 ml of N,N-dimethylformamide, 4.9 g of sodium azide was added at room temperature, followed by 4 hours' stirring at 80° C. under heating. The reaction liquid was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and resulting residue was purified by means of silica gel column chromatography (eluting solvent: from hexane to hexane/ethyl acetate=15/1) to provide 7.24 g of the title compound.
Aufarbeitung
- temperatureunder heating
- customThe reaction liquid
- washwashed successively with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customresulting residue
- customwas purified by means of silica gel column chromatography (eluting solvent: from hexane to hexane/ethyl acetate=15/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-fa934fb427fa461cb9c3ad4d8dbc1d09
- Quelldatensatz
- uspto-grants-2004_10
- Patentnummer
- US06809108B1
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