Trifluoroacetic acid → HCID 67441565, Verbindung

HRID 1801124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801124
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:10]([CH3:23])([CH3:22])[CH:9]2O)=[O:5])[CH3:2].FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:10]([CH3:22])([CH3:23])[CH2:9]2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67441733HCID 67441733, Verbindung

Produkt 1

HCID 67441565HCID 67441565, VerbindungAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12052TriethylsilaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a mixture of 4-hydroxy-3,3-dimethyl-2-pyridin-3-yl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (62.5 g, 200 mmol) and triethylsilane (50 mL) at 25° C. was added trifluoroacetic acid (25 mL) dropwise. The resulting mixture was stirred at 25° C. for 4 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with saturated aqueous sodium bicarbonate solution (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was triturated with methanol. The resulting precipitate was collected, dried in vacuo to afford 3,3-dimethyl-2-pyridin-3-yl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (15 g, 24%) as a white solid: LC/MS m/e calcd for C19H22N2O2 (M+H)+: 311.40, observed: 311.1.

Aufarbeitung

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate (2×200 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (2×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with methanol
  7. customThe resulting precipitate was collected
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2d07e36ef16a4334b97f16f463948944
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344137B2

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