反応 #2122485

反応方程式

(2,4,6-trimethylphenyl)-acetyl chloride

4-hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester

4-dimethylaminopyridine DMAP

→

1-methoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetoxy]-piperidine-4-carboxylic acid ethyl ester

溶媒

pyridine

反応条件

後処理

1. 1
   温度The reaction mixture was warmed up to room temperature
2. 2
   workup.WAITleft
3. 3
   濃縮Then the reaction mixture was concentrated
4. 4
   workup.ADDITIONcold (0° C.) water was added
5. 5
   抽出The aqueous phase was thoroughly extracted three times with dichloromethane
6. 6
   洗浄washed with brine
7. 7
   乾燥dried over sodium sulfate
8. 8
   濃縮concentrated
9. 9
   その他The crude product was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:4)

実験手順

To a solution of 4-hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester (0.5 g, 2.46 mmol) in 15 ml pyridine under argon was added 4-dimethylaminopyridine DMAP (0.11 g, 0.9 mmol). The solution was cooled down to 0° C., then (2,4,6-trimethylphenyl)-acetyl chloride (0.58 g, 2.95 mmol) was added dropwise. The reaction mixture was warmed up to room temperature and left stirring for 3 days. Then the reaction mixture was concentrated and cold (0° C.) water was added. The aqueous phase was thoroughly extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:4) to give pure 1-methoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetoxy]-piperidine-4-carboxylic acid ethyl ester (compound P3.6) as light yellow oil. Yield: 610 mg.

出典