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

Participants

Role	Name	HCID	Charge
Reactant	Formic Acid	HCID 284	—
Reactant	Nitrogen	HCID 947	—
Reactant	Diethyl Ether	HCID 3283	—
Reactant	(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one	HCID 11213668	—
Catalyst	Palladium	HCID 23938	—
Solvent	Water	HCID 962	—
Product	(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone	HCID 10780199	78%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Compound 4 (0.95 g, 2 mmol) and 10% Pd—C (0.02 mmol) were added to 20 mL of ether and the air was replaced with N2. Formic acid (94 mg, 2 mmol) was added and the mixture was stirred at 80° C. for 2 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 0.46 g of white solid in 78% yield. HPLC: 99.2%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658789B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-ed89e883fdb94f13b8d81c270874c11f
Source note	uspto-grants-2014_02