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

HRID 1801119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801119
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:9]([CH3:24])([CH3:23])[CH:8]2O)=[O:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)[C:9]([CH3:24])([CH3:23])[CH2:8]2)=[O:4]

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 674419164-Hydroxy-2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester

Produkt 1

HCID 674425662-(3-Methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl esterAusbeute 50 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred mixture solution of 4-hydroxy-2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (3.4 g, 10.2 mmol) and triethylsilane (6.0 mL) at 25° C. was added trifluoroacetic acid (3.0 mL) dropwise. The resulting mixture solution was stirred at 25° C. for 3 hours. 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 (4×100 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-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.6 g, 50%) as a white solid: LC/MS m/e calcd for C20H23NO3 (M+H)+: 326.41, observed: 326.2.

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 (4×100 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-257164ff32164a27a42af8803593a24f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344137B2

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