Trifluoroacetic acid → 2-(3-Bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

HRID 1800887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1800887
[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:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=1)[C:10]([CH3:24])([CH3:23])[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:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=1)[C:10]([CH3:23])([CH3:24])[CH2:9]2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 674413532-(3-Bromo-phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

Produkt 1

HCID 674428312-(3-Bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12052TriethylsilaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a mixture of 2-(3-bromo-phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (30 g, 74 mmol) and triethylsilane (50 mL) at 25° C. was added trifluoroacetic acid (15 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 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (15 g, 78%) as a white solid: LC/MS m/e calcd for C20H22BrNO2 (M+H)+: 389.31, observed: 390.0.

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-c178d3e319224bc0b1302d2c09572056
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344137B2

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