In a pressure tube, (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (100 mg), 2-chloro-5-(trifluoromethyl)pyridine (57 mg) and potassium carbonate (431 mg) were combined with toluene (1 ml) to give a yellow solution. The mixture was degassed by bubbling through argon for several minutes. BINAP (12 mg) and palladium(II)acetate (2 mg) were then added and the tube was sealed. The reaction mixture was stirred at 110° C. for 1 hour. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (SiO2; gradient: 0% to 40% EtOAc in hexane) to afford (S)-2,2-dimethyl-4-{2-[4-(5-trifluoromethyl-pyridin-2-ylamino)-phenyl]-ethyl}-oxazolidine-3-carboxylic acid tert-butyl ester (55 mg, 38%) as a yellow amorphous solid. MS (ISP): 466.3 ([M+H]+), 410.2 ([M+H—C4H8]+), 366.2 ([M+H—C4H8—CO2]+).
