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

HRID 245333Notes

Reaction equation

HRID 245333 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.CO.N#N.O.NN>[Pd].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

7

Reactant 4

HCID 887MethanolHCID 947NitrogenHCID 24654Hydrazine hydrate (1:1)HCID 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 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Compound 4 (0.95 g, 2 mmol) and 10% Pd—C (0.02 mmol) were added to 20 mL of methyl alcohol and the air was replaced with N2. Hydrazine hydrate (4 mmol) was added and on the mixture was stirred at 0° C. for 24 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 0.52 g of white solid in 88% yield. HPLC: 99%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d2ef23d9880242b39bc9fe6c93f221e2
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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