5-(2-Benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide → 5-(2-Hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide

Participants

Reaction Steps

To a stirred solution of 5-(2-benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.153 g, 0.00028 mole) in methanol (50 mL) was added 10% Pd/C (0.03 g) and the resulting mixture was stirred under an atmosphere of hydrogen for 3 hours. The mixture was then filtered through celite, the celite was washed with methanol and the organic layers were concentrated under reduced pressure. The resulting residue was purified by preparative HPLC to afford 0.055 g (43%) of 5-(2-hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 456.12 (M+1)+, 98.75%. 1H NMR (DMSO-d6): δ 10.8 (s, 1H), 8.7 (t, 1H), 7.8 (d, 1H), 7.4 (d, 1H), 7.24 (m, 3H), 7.12 (s, 1H), 7.04 (d, 1H), 6.92 (t, 2H), 4.7 (m, 1H), 4.2 (d, 2H), 3.7 (m, 2H), 3.4 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence