Reaktion #220782

Reaktionsgleichung

N-[3-(Trifluoromethyl)benzoyl]glycine

EDCI

1-hydroxybenzotriazole hydrate

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

→

1-(tert-butoxycarbonyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine

Ausbeute 85.0%

Lösungsmittel

dichloromethane

triethylamine

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   ExtraktionThe obtained mixture was extracted with dichloromethane (50 mLX 2)
3. 3
   Waschenwashed with H2O (50 mL×2) and brine (50 mL)
4. 4
   Trocknendried (over MgSO4)
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto thereby afford a yellow oil
7. 7
   SonstigeThe obtained crude product
8. 8
   Sonstigewas purified by column chromatography (SiO2,70% ethyl acetate-hexane)

Vorschrift

N-[3-(Trifluoromethyl)benzoyl]glycine (4.22 g, 17.0 mmol), EDCI (4.25 g, 22.1 mmol), 1-hydroxybenzotriazole hydrate (2.99 g, 22.1 mmol) and triethylamine (1.72 g) were added to an anhydrous dichloromethane (200 mL) solution of 1-(tert-butoxycarbonyl)-4-(aminomethyl)piperidine (4.03 g). The resulting reaction mixture was stirred at 25° C. for 20 hours, and H2O (100 mL) was then added to the mixture. The obtained mixture was extracted with dichloromethane (50 mLX 2). The extracts were combined, washed with H2O (50 mL×2) and brine (50 mL), dried (over MgSO4) and concentrated to thereby afford a yellow oil. The obtained crude product was purified by column chromatography (SiO2,70% ethyl acetate-hexane) to provide 1-(tert-butoxycarbonyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine as a white solid (6.39 g, 85%). 1H NMR (CDCl3, 300 MHz) δ 1.4 (s, 9H), 1.0-1.8 (m, 5H), 2.6-2.8 (m, 2H), 3.15-3.3 (m, 2H), 4.0-4.3 (m, 4H), 6.6-6.7 (m, 1H), 7.64 (s, 1H), 7.60 (dd, 1H, J=7.2, 7.2 Hz), 7.79 (d, 1H, J=7.2 Hz), 8.0 (d, 1H, J=7.2 Hz), 8.11 (s, 1H). The purity was determined by RPLC/MS (97%). ESI/MS m/e 444.3 (M++H, C21H28N3O4).

Quelle