반응 #220786

반응 방정식

NaOH

Triethylamine

N-(benzyloxycarbonyl)glycine

EDCI

HOBt

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

→

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

수율 94.0%

용매

chloroform

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   추출the aqueous layer was extracted with dichloromethane (100 mLX 3)
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The obtained crude product
7. 7
   기타was purified by column chromatography (SiO2, ethyl acetate)

실험 절차

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%).

출처