반응 #2122485

반응 방정식

(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

용매

pyridine

반응 조건

후처리

1. 1
   온도The reaction mixture was warmed up to room temperature
2. 2
   workup.WAITleft
3. 3
   농축Then the reaction mixture was concentrated
4. 4
   workup.ADDITIONcold (0° C.) water was added
5. 5
   추출The aqueous phase was thoroughly extracted three times with dichloromethane
6. 6
   세척washed with brine
7. 7
   건조dried over sodium sulfate
8. 8
   농축concentrated
9. 9
   기타The crude product was purified by column chromatography on silica gel (ethyl acetate/cyclohexane 1:4)

실험 절차

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.

출처