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

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Nitrogen	HCID 947	—
Reactant	(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one	HCID 11213668	—
Catalyst	Palladium	HCID 23938	—
Solvent	Water	HCID 962	—
Solvent	Triethylammonium formate	HCID 11084032	—
Product	(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone	HCID 10780199	84%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Compound 4 (0.95 g, 2 mmol) and 10% Pd—C (1 mmol) were added to the mixture of 20 mL of ethanol and 2 mL of water and the air was replaced with N2. The triethylamine-Formic acid azeotrope (704 mg, 4 mmol) was added and the mixture was stirred at 80° C. for 12 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 0.49 g of white solid in 84% yield. HPLC: 99.3%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658789B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-9639805796db427d8847975baf2f6e04
Source note	uspto-grants-2014_02