تفاعل #420161

معادلة التفاعل

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

NaH

2,6-dinitrobenzonitrile

→

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

المردود 70.6%

المذيبات

water

THF

THF

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرى20 min
2. 2
   أخرىat room temperature
3. 3
   استخلاصextracted with EtOAc
4. 4
   غسيلthe combined organic phases were washed with brine
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated
8. 8
   أخرىThe residue was purified by Biotage purification system (120 g Silicycle column, Hexane:EtOAc=3:2 as eluent)

الإجراء التجريبي

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]+.

المصدر