반응 #420161

반응 방정식

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

NaH

2,6-dinitrobenzonitrile

→

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

수율 70.6%

용매

water

THF

THF

DMF

반응 조건

후처리

1. 1
   기타20 min
2. 2
   기타at room temperature
3. 3
   추출extracted with EtOAc
4. 4
   세척the combined organic phases were washed with brine
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue was purified by Biotage purification system (120 g Silicycle column, Hexane:EtOAc=3:2 as eluent)

실험 절차

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]+.

출처