Hydrazine → HCID 68776545, compound

Participants

Reaction Conditions

Reaction Steps

Anhydrous hydrazine (0.30 mL, 9.56 mmol) was added to a solution of the product of Example 2A (0.79 g, 2.81 mmol) in toluene (10 mL). The solution was stirred at 20-25° C. for 10 hours, then diluted with toluene (15 mL) and heated at reflux under a Dean-Stark trap for 33 hours. The solution was cooled to room temperature and concentrated under vacuum to leave a white solid residue. The residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc 70:30-50:50) to provide the title compound as a white solid (0.79 g, 72% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.64-1.78 (m, 4H), 2.05 (dd, J=10.5, 2.7 Hz, 2H), 2.08-2.18 (m, 2H), 2.40 (br s, 2H), 2.45-2.55 (m, 2H), 2.96 (t, J=6.6 Hz, 1H), 4.73 (s, 2H), 7.44 (ddd, J=8.1, 6.4, 1.7 Hz, 1H), 7.66-7.77 (m, 2H), 8.24 (ddd, J=8.0, 1.4, 0.7 Hz, 1H); MS (DCI) m/z 282 (M+H)+.

Provenance & Evidence