تفاعل #329744

معادلة التفاعل

3,3-Dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester

4-chlorophenylmagnesium bromide

→

title compound

4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to about room temperature
2. 2
   أخرىThe reaction was quenched with aqueous ammonium chloride
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   تركيزThe combined organic layers were concentrated in vacuo
5. 5
   أخرىpurified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

الإجراء التجريبي

To an ice-cooled solution 3,3-Dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.6 g, 7.2 mmol) in THF (20 mL) was added 4-chlorophenylmagnesium bromide (1 M in ether, 15 mL, 15 mmol). The solution was allowed to warm to about room temperature, then stirred at room temperature for about 22 hours. The reaction was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, then purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate) to yield the title compound as a colorless oil.

المصدر