反应 #420161

反应方程式

tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate

NaH

2,6-dinitrobenzonitrile

→

tert-butyl 2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate

收率 70.6%

溶剂

water

THF

THF

DMF

反应条件

后处理

1. 1
   其他20 min
2. 2
   其他at room temperature
3. 3
   萃取extracted with EtOAc
4. 4
   洗涤the combined organic phases were washed with brine
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   其他evaporated
8. 8
   其他The residue was purified by Biotage purification system (120 g Silicycle column, Hexane:EtOAc=3:2 as eluent)

实验过程

To a solution of tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate (0.86 g, 4 mmol) in dry THF (30 mL) was added at −20° C. NaH (0.32 g, 8 mmol) and the mixture was stirred 10 min at −20° C. and then 20 min at room temperature. The reaction mixture was then cooled to −20° C. and 2,6-dinitrobenzonitrile (0.772 g, 4 mmol) in dry THF (10 mL) and DMF (1 mL) was added dropwise over 15 min period. The solution was stirred under nitrogen at room temperature for 18 hours, diluted with water and extracted with EtOAc, the combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by Biotage purification system (120 g Silicycle column, Hexane:EtOAc=3:2 as eluent) to give tert-butyl 2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate (1.02 g, 70.6%). MS 262 [M+H-Boc]+.

来源