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

HRID 245319Notes

Reaction equation

HRID 245319 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-40566736bbfb4d2a8947a776376ad043
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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