Reacción #53317

Ecuación de reacción

water

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

4-chloropyridine 1-oxide

sodium hydrogencarbonate

→

title compound

Rendimiento 36.8%

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

Rendimiento 36.8%

Disolventes

isoamyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturaunder reflux for 4 hours
3. 3
   Temperaturato cool
4. 4
   ExtracciónThe reaction mixture was extracted with methylene chloride
5. 5
   Lavadothe organic layer was washed with saturated sodium chloride solution
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   Otrothe resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

Procedimiento

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).

Fuente