Diisopropylethylamine → HCID 89814115, compound

Participants

Reaction Steps

To a vial charged with (S)-3-(4-aminocyclohexyl)-4-(4-fluorophenyl)-5,5-dimethyloxazolidin-2-one (0.353 g, 1.152 mmol) were added ACN (3.84 mL), DIEA (0.402 mL, 2.304 mmol) and 4-fluoro-3-nitrobenzonitrile (commercially available from J & W Pharmlab, Levittown, Pa.) (0.191 g, 1.152 mmol) respectively. After completion of reaction, the dark mixture was dried under reduced pressure and purified with a 25 g HP spherical silica column ramping DCM:MeOH (90:10) in DCM from 0-50%, then isocratic at 50% (detection at 215 nm) leading to isolation of product which was obtained as an orange/brown oil as a mixture of cis/trans isomers of (S)-4-((4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)cyclohexyl)amino)-3-nitrobenzonitrile (0.490 g, 1.083 mmol, 94% yield). m/z (ESI) 453.2 (M+H)+.

Provenance & Evidence