Reaktion #220772

Reaktionsgleichung

N-(9-fluorenylmethyloxycarbonyl)glycine

EDCI

HOBt

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

→

1-(tert-butoxycarbonyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine

Ausbeute 44.0%

Lösungsmittel

dichloromethane

Triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   Waschenwashed with water (100 mL×3) and brine (100 mL×2)
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated
5. 5
   Sonstigerecrystallized from acetonitrile/methanol (150 mL/1 mL) at 0° C.

Vorschrift

Triethylamine (3.51 g), N-(9-fluorenylmethyloxycarbonyl)glycine (7.93 g, 26.7 mmol), EDCI (3.80 g) and HOBt (4.33 g) were added to a dichloromethane (150 mL) solution of 4-(aminomethyl)-1-(tert-butoxycarbonyl)piperidine (5.72 g). The resulting reaction mixture was stirred at room temperature for 18 hours, then washed with water (100 mL×3) and brine (100 mL×2), dried over anhydrous sodium sulfate, concentrated and recrystallized from acetonitrile/methanol (150 mL/1 mL) at 0° C. to provide 1-(tert-butoxycarbonyl)-4-[[N-(9-fluorenylmethyloxycarbonyl)glycyl]aminomethyl]piperidine (5.75 g, 44%) as an off-white crystal.

Quelle