تفاعل #2122484

معادلة التفاعل

water

4-dimethylaminopyridine DMAP

4-hydroxy-1-methoxy-piperidine-4-carbonitrile

(2,4,6-trimethyl-phenyl)-acetyl chloride

→

(2,4,6-trimethyl-phenyl)-acetic acid 4-cyano-1-methoxy-piperidin-4-yl ester

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.WAIT30 minutes at 0° C. and finally left
3. 3
   workup.STIRRINGstirring overnight at room temperature
4. 4
   استخلاصextracted three times with dichloromethane
5. 5
   تجفيفThe combined organic layers were dried over sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under vacuum
8. 8
   أخرىThe crude product was purified by column chromatography on silica gel

الإجراء التجريبي

To a cooled (−20° C.) solution of 4-hydroxy-1-methoxy-piperidine-4-carbonitrile (0.32 g, 2.05 mmol) in 2 ml dichloromethane was added 4-dimethylaminopyridine DMAP (13 mg, 0.05 mmol) under argon. Then (2,4,6-trimethyl-phenyl)-acetyl chloride (0.52 g, 2.64 mmol) dissolved in dichloromethane (3 ml) was added dropwise. The reaction mixture was stirred at −20° C. for 30 minutes, then 30 minutes at 0° C. and finally left stirring overnight at room temperature. The reaction mixture was poured into water and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel to give pure (2,4,6-trimethyl-phenyl)-acetic acid 4-cyano-1-methoxy-piperidin-4-yl ester (compound P3.5) as white solid, mp 75-78° C. Yield: 480 mg.

المصدر