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

HRID 245318Notes

Reaction equation

HRID 245318 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.N#N.[H][H]>[Pd].C(OCC)(=O)C>[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 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinoneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (0.95 g, 2 mmol) and 0.5 g of 10 wt % Pd—C were added to 20 mL ethyl acetate and the air was replaced with N2. Hydrogen was passed into the mixture and the mixture was heated to 50° C. and reacted for 20 hours. Filtered and the solvent was evaporated to provide 0.53 g of white solid in 90% yield.

Workup

  1. customreacted for 20 hours
  2. filtrationFiltered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-27dfd314e3fe4a93b72d2df5917b9768
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

Loading…