Reaktion #976869

Reaktionsgleichung

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe system was flushed with nitrogen
2. 2
   TemperaturThe system was cooled to room temperature
3. 3
   Sonstigequenched by slow addition of water
4. 4
   ExtraktionThe mixture was extracted with EtOAc (3×20 mL)
5. 5
   WaschenThe organic phase was washed with saturated NaHCO3 solution and brine
6. 6
   TrocknenThe organic fraction was dried (MgSO4)
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe crude mixture was purified by ISCO column chromatography

Vorschrift

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.

Quelle