Benzyl Alcohol → HCID 11606270, compound

Participants

Reaction Steps

Diphenylphosphoryl azide (0.070 mL, 0.324 mmol) was added to a solution of 4-[4-benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-bicyclo[2.2.2]octane-1-carboxylic acid (see Example 22; 0.140 g, 0.324 mmol) and diisopropylethylamine (0.068 mL, 0.39 mmol) in toluene (5 mL). The mixture was stirred for 2 hours. Benzyl alcohol (0.067 mL, 0.648 mmol) was added to the mixture. The mixture was stirred at room temperature for 18 hours. Solvent was removed. The mixture was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.002 g (1%) of the title compound as a yellow solid. MS (ESP+) m/z 537.4 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.71 (m, 1H), 7.33 (m, 5H), 7.22 (m, 2H), 6.97 (m, 3H), 6.05 (s, 2H), 5.02 (s, 2H), 2.63 (s, 3H), 2.17 (m, 6H), 2.06 (m, 6H).

Provenance & Evidence