Water → HCID 58415410, compound

Participants

Reaction Steps

To a solution of 5-allyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (150 mg) in acetone (5.5 mL) was added water (1 mL) followed by NMO (60 mg) and OsO4 (0.536 mL, 2.5% in tert-BuOH). After stirring at room temperature for 24 h, 100 mg NMO and 0.1 mL OsO4 solution were added. After 9 h 0.1 mL more OsO4 solution was added and stirred at room temperature over the weekend. The reaction was then quenched with 1:1 aqueous saturated NaHCO3:Na2SO3 and partitioned between aqueous saturated NaHCO3 and EtOAc. Aqueous layer was extracted with EtOAc (3×). Combined organic layers were dried over Na2SO4 and concentrated. Purification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-40% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min) to give title compound as a white solid. Mass. found (M+H)+, 387.0.

Provenance & Evidence