Реакция #976869

Уравнение реакции

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

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеThe system was flushed with nitrogen
2. 2
   ТемператураThe system was cooled to room temperature
3. 3
   Другоеquenched by slow addition of water
4. 4
   ЭкстракцияThe mixture was extracted with EtOAc (3×20 mL)
5. 5
   ПромывкаThe organic phase was washed with saturated NaHCO3 solution and brine
6. 6
   СушкаThe organic fraction was dried (MgSO4)
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеThe crude mixture was purified by ISCO column chromatography

Методика

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.

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