Stannous Chloride → (S)-3-Amino-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)benzonitrile

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Reaction Conditions

Reaction Steps

To a flask charged with (S)-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)-3-nitrobenzonitrile (0.490 g, 1.083 mmol) was added EtOH (4.33 mL) followed by tin (II) chloride (0.616 g, 3.25 mmol). The resulting yellow suspension was heated overnight at 80° C. LC-MS analysis of the resulting suspension indicated about 90% conversion to the desired product (215 nm). Additional EtOH (4 mL) was added to aid solubilization and additional SnCl2 was added (300 mg). The resulting mixture was heated at 80° C. After 1 hour, LC-MS indicated complete conversion. The yellow suspension was dried under reduced pressure and the residue was purified with a 50 g SNAP column ramping DCM:MeOH (90:10) in DCM (0-30%, then isocratic at 30%, detection at 215 nm) to provide (S)-3-amino-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)benzonitrile (0.156 g, 0.369 mmol, 34.1% yield) as a brown oil and as a mixture of isomers with impurities present (˜20% based on LC-MS). The material was used in the next step without further purification. m/z (ESI) 423.2 (M+H)+.

Provenance & Evidence