反応 #53317

反応方程式

water

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

4-chloropyridine 1-oxide

sodium hydrogencarbonate

→

title compound

収率 36.8%

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

収率 36.8%

溶媒

isoamyl alcohol

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度under reflux for 4 hours
3. 3
   温度to cool
4. 4
   抽出The reaction mixture was extracted with methylene chloride
5. 5
   洗浄the organic layer was washed with saturated sodium chloride solution
6. 6
   乾燥dried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   その他the resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

実験手順

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).

出典