(4S,5R)-3-{[6-azetidin-1-yl-3-(2-methoxy-5-nitrophenyl)pyridin-2-yl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one → (4S,5R)-3-{[3-(5-amino-2-methoxyphenyl)-6-azetidin-1-ylpyridin-2-yl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

To a solution of (4S,5R)-3-{[6-azetidin-1-yl-3-(2-methoxy-5-nitrophenyl)pyridin-2-yl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (1.26 g, 2.064 mmol) in EtOH (80 mL) was added Pd—C (10%) (0.220 g, 0.206 mmol). The mixture was subjected to hydrogenation by using a Hz balloon for 6.5 h. The mixture was filtered through Celite® and the filtrate was concentrated in vacuo. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 260 mL, gradient to 50% EtOAc in hexanes over 2240 mL) to afford (4S,5R)-3-{[3-(5-amino-2-methoxyphenyl)-6-azetidin-1-ylpyridin-2-yl]methyl}-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one. LCMS calc.=580.2. found=581.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.86 (s, 1H); 7.75 (s, 2H); 7.32 (d, J=8.3 Hz, 1H); 6.79 (d, J=8.6 Hz, 1H); 6.68 (dd, J=8.6, 2.9 Hz, 1H); 6.54 (d, 2.9 Hz, 1H); 6.27 (d, J=8.3 Hz, 1H); 5.61 (d, J=8.5 Hz, 1H); 4.93-4.30 (m, 1H); 4.18-4.01 (m, 6H); 3.70 (s, 3H); 3.51 (s, br, 2H); 2.46-2.37 (m, 2H); 0.68 (s, br, 3H).

Provenance & Evidence