HCID 86644572, compound → HCID 86644571, compound

Participants

Reaction Steps

To a degassed solution of the title compound from Example 8 Step E (549 mg, 0.79 mmol) in EtOAc (15 mL) was added platinum(IV) oxide (200 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 20 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. The filtrate was then concentrated in vacuo. Purification by chromatography on silica gel (0 to 40% EtOAc in hexanes, then 40 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 700.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.21 (s, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.86-7.82 (m, 2H), 7.38-7.35 (m, 2H), 7.30 (d, J=8.0 Hz, 2H), 7.19 (d, J=8.0 Hz, 2H), 7.09-7.06 (m, 2H), 5.12 (s, 2H), 4.37 (q, J=7.0 Hz, 2H), 4.29-4.20 (br m, 2H), 2.83-2.76 (br m, 2H), 2.68-2.63 (m, 1H), 1.84-1.81 (m, 2H), 1.49 (s, 9H), 1.38 (t, J=7.0 Hz, 3H).

Provenance & Evidence