HCID 53242202, compound → HCID 53251117, compound

Participants

Reaction Steps

Adam's catalyst (PtO2, 17 mg, 0.075 mmol; Aldrich) was added to a solution of the product of Example 1C (170 mg, 0.56 mmol) in ethanol (20 mL). The reaction flask was evacuated and purged with nitrogen (3 cycles) then evacuated and purged with hydrogen (4 cycles), and the mixture was stirred under hydrogen (1 atm) at room temperature for 18 hours. The flask was evacuated and purged with nitrogen (3 cycles), and the reaction mixture was filtered. The filtrate was concentrated under vacuum, and the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-100% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.45 (s, 3H), 2.54 (s, 3H), 2.84-3.03 (m, 6H), 3.06-3.15 (m, 2H), 3.67 (s, 2H), 6.74-6.78 (m, 1H), 6.83-6.91 (m, 1H), 7.14 (d, J=7.9 Hz, 1H), 7.18 (dd, J=7.9, 1.2 Hz, 1H), 7.49 (dd, J=7.9, 2.0 Hz, 1H), 8.13 (d, J=2.0 Hz, 1H); MS (APCI) m/z 306 (M+H)−.

Provenance & Evidence