1,1-Dimethylethyl 4-(1,2-dihydro-2-oxo-3-quinolinyl)-4-hydroxy-1-piperidinecarboxylate → 3-(4-Hydroxypiperidin-4-yl)quinolin-2(1H)-one

HRID 501950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501950
[OH:1][C:2]1([C:15]2[C:16](=[O:25])[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1>FC(F)(F)C(O)=O>[OH:1][C:2]1([C:15]2[C:16](=[O:25])[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Komponenten

3

Edukt 1

HCID 594243951,1-Dimethylethyl 4-(1,2-dihydro-2-oxo-3-quinolinyl)-4-hydroxy-1-piperidinecarboxylate

Produkt 1

HCID 594242883-(4-Hydroxypiperidin-4-yl)quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 4-hydroxy-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (300 mg, 0.87 mmol) was dissolved in trifluoroacetic acid (50% in dichloromethane, 6 mL). The reaction was stirred 30 min and concentrated. The residue was dissolved in water, extracted with dichloromethane (2×) which were discarded. The aqueous was made basic with solid potassium carbonate. The resulting solid was filtered to give 145 mg (68%) as a white powder. Mass spec.: 245.35 (MH)+.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane (2×) which
  4. filtrationThe resulting solid was filtered
  5. customto give 145 mg (68%) as a white powder

Quellen und Nachweise

ORD-Eintrag
ord-6fd1ec206a9841c799e01aa838867805
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772244B2

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