反应详情

A mixture of tert-butyl 4-(2-fluoro-5-iodo-4-methoxyphenyl)piperidine-1-carboxylate (58 mg; 0.133 mmol) and (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (111 mg, 0.187 mmol) was treated with 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (˜10 mg) as described earlier. The product was purified by chiral HPLC (ChiralPak OD column, 10% IPA/heptane) to afford tert-butyl 4-[2′-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-fluoro-6-methoxy-4′-(trifluoromethyl)biphenyl-3-yl]piperidine-1-carboxylate as a colorless glass. LCMS=678.8 (M+1-100)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers) δ 7.86 (s, 1 H), 7.69 (s, 2 H), 7.64-7.61 (m, 2 H), 7.32 (d, J=8 Hz, 1 H), 6.96 (d, J=8.4 Hz, 1 H), 6.70 (d, J=11.9 Hz, 1 H), 5.57 (d, J=8 Hz, 1 H), 4.88 (d, J=15.8 Hz, 1 H), 4.26-4.17 (m, 2 H), 3.86 (d, J=15.8 Hz, 1H), 3.83-3.78 (m, 1 H), 3.77 (s, 3 H), 3.01-2.93 (m, 1 H), 2.84-2.75 (m, 2 H), 1.84-1.69 (m, 2 H), 1.64-1.50 (m, 2 H), 1.45 (s, 9H), 0.38 (d, J=6.7 Hz, 3 H).

1. customThe product was purified by chiral HPLC (ChiralPak OD column, 10% IPA/heptane)