tert-Butyl 4-(4-((2-(6-(4-(ethoxycarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-4-methylphenoxy)methyl)phenyl)-3,6-dihydropyridine-1 (2H)-carboxylate → tert-Butyl 4-(4-((2-(6-(4-(ethoxycarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-4-methylphenoxy)methyl)phenyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a degassed solution of the title compound from Example 12 Step D (365 mg, 0.551 mmol) in EtOAc (10 mL) was added platinum(IV) oxide (125 mg). The reaction flask was fitted with a hydrogen balloon attached to a 3-way adapter. The reaction mixture was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, and was stirred vigorously. After 40 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. Purification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes, then 50 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 665.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=8.0 Hz, 1 H), 8.12 (s, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.79 (br s, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 2H), 7.19-7.16 (m, 3H), 6.97 (d, J=8.5 Hz, 1H), 5.09 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 4.30-4.18 (m, 2H), 2.82-2.78 (m, 2H), 2.67-2.62 (m, 1H), 2.35 (s, 3H), 1.83-1.80 (m, 2H), 1.66-1.57 (m, 2H), 1.49 (s, 9H), 1.40 (t, J=7.0 Hz, 3H).

Provenance & Evidence