反応 #329744

反応方程式

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

溶媒

THF

反応条件

後処理

1. 1
   温度to warm to about room temperature
2. 2
   その他The reaction was quenched with aqueous ammonium chloride
3. 3
   抽出extracted with ethyl acetate
4. 4
   濃縮The combined organic layers were concentrated in vacuo
5. 5
   その他purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

実験手順

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.

出典