تفاعل #220782

معادلة التفاعل

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

المردود 85.0%

المذيبات

dichloromethane

triethylamine

H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   استخلاصThe obtained mixture was extracted with dichloromethane (50 mLX 2)
3. 3
   غسيلwashed with H2O (50 mL×2) and brine (50 mL)
4. 4
   تجفيفdried (over MgSO4)
5. 5
   تركيزconcentrated
6. 6
   أخرىto thereby afford a yellow oil
7. 7
   أخرىThe obtained crude product
8. 8
   أخرىwas purified by column chromatography (SiO2,70% ethyl acetate-hexane)

الإجراء التجريبي

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).

المصدر