Reacción #309588

Ecuación de reacción

benzyl 4-{4-[({2-[(tert-butoxycarbonyl)amino]phenyl}amino)carbonyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate

hydrogen

diethyl ether ethyl acetate

→

title compound

Rendimiento 81.0%

tert-Butyl {2-[(4-piperidin-4-ylbenzoyl)amino]phenyl}carbamate

Rendimiento 81.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Filtraciónfiltered through a pad of celite
3. 3
   Otrothe solvent evaporated under reduced pressure
4. 4
   OtroThe resultant foam was triturated under diethyl ether
5. 5
   Filtraciónfiltered
6. 6
   Otroto give a white solid
7. 7
   Filtraciónthen collected by suction filtration
8. 8
   LavadoThis solid was washed with diethyl ether, isohexane
9. 9
   Otrodried in vacuo

Procedimiento

To a solution of benzyl 4-{4-[({2-[(tert-butoxycarbonyl)amino]phenyl}amino)carbonyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate (269 g, 524 mmol; prepared as described in Method 2 below) in methanol (3000 ml) was added 10% palladium on charcoal (10 g). The reaction mixture was placed under 5 bar pressure of hydrogen gas and heated to 50° C. for 1 h. The reaction mixture was cooled to room temperature, filtered through a pad of celite and the solvent evaporated under reduced pressure. The resultant foam was triturated under diethyl ether and filtered to give a white solid. This product was ground finely and stirred with 95:5 diethyl ether/ethyl acetate then collected by suction filtration. This solid was washed with diethyl ether, isohexane and dried in vacuo to afford the title compound (167 g, 81%); NMR Spectrum: (DMSO-d6) 1.45 (s, 9H), 1.57 (m, 2H), 1.72 (m, 2H), 2.61 (t, 2H), 2.69 (m, 1H), 3.07 (m, 2H), 7.18 (m, 2H), 7.40 (d, 2H), 7.53 (d, 2H), 7.91 (d, 2H), 8.70 (br s, 1H), 9.82 (br s, 1H); Mass Spectrum: M+H+396.

Fuente