반응 #53317

반응 방정식

water

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

4-chloropyridine 1-oxide

sodium hydrogencarbonate

→

title compound

수율 36.8%

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

수율 36.8%

용매

isoamyl alcohol

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도under reflux for 4 hours
3. 3
   온도to cool
4. 4
   추출The reaction mixture was extracted with methylene chloride
5. 5
   세척the organic layer was washed with saturated sodium chloride solution
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   기타the resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

실험 절차

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).

출처