Reacción #976869

Ecuación de reacción

4-methyl-2-(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl

2-ethyl-piperidine

NaOtBu

→

2-[5-(2-ethyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe system was flushed with nitrogen
2. 2
   TemperaturaThe system was cooled to room temperature
3. 3
   Otroquenched by slow addition of water
4. 4
   ExtracciónThe mixture was extracted with EtOAc (3×20 mL)
5. 5
   LavadoThe organic phase was washed with saturated NaHCO3 solution and brine
6. 6
   SecadoThe organic fraction was dried (MgSO4)
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe crude mixture was purified by ISCO column chromatography

Procedimiento

To a solution of 4-methyl-2-(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester, 1g (250 mg, 0.49 mmol) in toluene (5 mL) in a sealed tube was added racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (59 mg, 0.15 mmol), Pd(OAc)2 (110 mg, 0.49 mmol), 2-ethyl-piperidine (83 mg, 0.73 mmol). The system was flushed with nitrogen. To this was added NaOtBu (70 mg, 0.73 mmol) and heated to 100° C. for 3 h. The system was cooled to room temperature and quenched by slow addition of water. The mixture was extracted with EtOAc (3×20 mL). The organic phase was washed with saturated NaHCO3 solution and brine. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by ISCO column chromatography to obtain 2-[5-(2-ethyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester. Calcd for C28H36F3NO2 (M+H) 476.59, Found 476.38.

Fuente