2-Ethylpiperidine → HCID 57665995, Verbindung

HRID 889687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889687
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:13]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.[CH2:64]([CH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][NH:67]1)[CH3:65].CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=2)[CH:13]=[C:14]([N:67]2[CH2:68][CH2:69][CH2:70][CH2:71][CH:66]2[CH2:64][CH3:65])[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Komponenten

7

Edukt 4

HCID 942052-EthylpiperidineHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 23676156Sodium t-butoxideHCID 577550554-Methyl-2-(5-trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Produkt 1

HCID 57665995HCID 57665995, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe system was flushed with nitrogen
  2. temperatureThe system was cooled to room temperature
  3. customquenched by slow addition of water
  4. extractionThe mixture was extracted with EtOAc (3×20 mL)
  5. washThe organic phase was washed with saturated NaHCO3 solution and brine
  6. dry with materialThe organic fraction was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by ISCO column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-427cf787464c48b9bba69754ff6d0129
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252935B2

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