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

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Nitrogen	HCID 947	—
Reactant	Hydrazine hydrate (1:1)	HCID 24654	—
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	88%

Reaction Conditions

Temperature	0 °C

Reaction Steps

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%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08658789B2
Source dataset	uspto-grants-2014_02
ORD ID	ord-d2ef23d9880242b39bc9fe6c93f221e2
Source note	uspto-grants-2014_02