Reaktion #74456

Reaktionsgleichung

NMO

NMO

5-allyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole

water

→

title compound

3-[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]propane-1,2-diol

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature over the weekend
2. 2
   SonstigeThe reaction was then quenched with 1:1 aqueous saturated NaHCO3
3. 3
   SonstigeNa2SO3 and partitioned between aqueous saturated NaHCO3 and EtOAc
4. 4
   ExtraktionAqueous layer was extracted with EtOAc (3×)
5. 5
   TrocknenCombined organic layers were dried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-40% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min)

Vorschrift

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.

Quelle