Nitrogen → (5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

HRID 245319

Reaktionsgleichung

Reaktionsgleichung von HRID 245319
C([N:8]([CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1)CC1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+].N#N>[Pd].CC(C)=O>[NH2:8][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 2723923Ammonium formateHCID 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

Produkt 1

HCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinoneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (0.95 g, 2 mmol), 0.5 g 10 wt % Pd—C and ammonium formate (1.3 g, 20 mmol) were added to 20 mL acetone and the air was replaced with N2. The mixture was heated to reflux and stirred for 10 hours. The mixture was filtered and separated by water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated to provide 0.52 g of white solid in 88% yield.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe mixture was filtered
  4. customseparated by water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-40566736bbfb4d2a8947a776376ad043
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658789B2

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