Reaktion #53317

Reaktionsgleichung

water

4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine

4-chloropyridine 1-oxide

sodium hydrogencarbonate

→

title compound

Ausbeute 36.8%

4-[4-(t-butoxycarbonylamino)methyl-4-hydroxypiperidin-1-yl]pyridine 1-oxide

Ausbeute 36.8%

Lösungsmittel

isoamyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturunder reflux for 4 hours
3. 3
   Temperaturto cool
4. 4
   ExtraktionThe reaction mixture was extracted with methylene chloride
5. 5
   Waschenthe organic layer was washed with saturated sodium chloride solution
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   Sonstigethe resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

Vorschrift

To a suspension in isoamyl alcohol (35 ml) of conventionally known compounds: 4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine (2.00 g) and 4-chloropyridine 1-oxide (1.12 g), was added sodium hydrogencarbonate (1.75 g) and the mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool and water was added thereto. The reaction mixture was extracted with methylene chloride and the organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1) to obtain the title compound (1.03 g).

Quelle