تفاعل #220786

معادلة التفاعل

NaOH

Triethylamine

N-(benzyloxycarbonyl)glycine

EDCI

HOBt

4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine

→

4-[[(N-(benzyloxycarbonyl) glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine

المردود 94.0%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic layer was separated
2. 2
   استخلاصthe aqueous layer was extracted with dichloromethane (100 mLX 3)
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe obtained crude product
7. 7
   أخرىwas purified by column chromatography (SiO2, ethyl acetate)

الإجراء التجريبي

Triethylamine (2.8 mL, 20 mmol), N-(benzyloxycarbonyl)glycine (3.77 g, 18 mmol), EDCI (3.45 g, 18 mmol) and HOBt (2.43 g, 18 mmol) were added to a chloroform (80 mL) solution of 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine (3.54 g, 16.5 mmol). The resulting mixture was stirred at room temperature for 15 hours, and a 2 M aqueous solution of NaOH (100 mL) was then added to the mixture. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (100 mLX 3). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The obtained crude product was purified by column chromatography (SiO2, ethyl acetate) to provide 4-[[(N-(benzyloxycarbonyl) glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine as an amorphous solid (6.27 g, 94%).

المصدر