Réaction #220786

Équation de réaction

NaOH

Triethylamine

N-(benzyloxycarbonyl)glycine

EDCI

HOBt

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

→

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

Rendement 94.0%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer was separated
2. 2
   Extractionthe aqueous layer was extracted with dichloromethane (100 mLX 3)
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   AutreThe obtained crude product
7. 7
   Autrewas purified by column chromatography (SiO2, ethyl acetate)

Mode opératoire

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%).

Source