Reaction Steps
(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-(2-bromo-5-nitrobenzyl)-4-methyl-1,3-oxazolidin-2-one (42 mg, 0.083 mmol), 3-methylpiperidine (13 mg, 0.126 mmol), palladium(II) acetate (1.0 mg, 5%), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (2-6 mg, 7.5%), cesium carbonate (55 mg, 0.17 mmol) and THF (1 mL) were sealed in a microwave vessel. The reaction mixture was irradiated by microwave at 150° C. for 1 hour. Reaction crude was purified by SiO2 to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(3-methylpiperidin-1-yl)-5-nitrobenzyl]-1,3-oxazolidin-2-one. LCMS calc.=546.17; found=546.23 (M+1)+. 1H NMR signals are doubled because of atropoisomerism 1H NMR (CDCl3, 500 MHz) δ 8.22 (d, J=2.5 Hz, 1H), 8.16 (d, J=3 Hz, 0.5H), 8.14 (d, J=2.5 Hz, 0.5H), 7.89 (s, 1H), 7.78 (s, 2H), 7.14 (d, J=4 Hz, 0.5H), 7.12 (d, J=4.0 Hz, 0.5H), 5.76 (d, J=8 Hz, 1H), 4.84 (d, J=4.5 Hz, 0.5H), 4.81 (d, J=4.5 Hz, 0.5H), 4.40 (d, J=3.5 Hz, 0.5H), 4.36 (d, J=3.5 Hz, 0.5H), 3.87-3.83 (m, 1H), 7.14 (s, 1H), 3.09 (s, 2H), 3.02 (d, J=12.5 Hz, 1H), 2.84 (t, J=10 Hz, 1H), 2.60 (t, J=12.5 Hz, 1H), 2.54 (t, J=11 Hz, 0.5H), 2.33 (t, J=11 Hz, 1H), 1.16-1.07 (m, 1H), 0.96 (d, J=6.5 Hz, 0.5H), 0.94 (d, J=6.5 Hz, 1.5H), 0.70 (s, 1.5H), 0.69 (s, 1.5H).
