Sodium Carbonate → tert-butyl 5-oxido-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

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Reaction Steps

mCPBA (26.1 g of 77% pure material, 118 mmol) was added in small portions to a solution of tert-butyl 10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (29.54 g, 91.06 mmol) in chloroform (500 mL), and the reaction was stirred for one hour at ambient temperature. Aqueous sodium carbonate (400 mL of a 1% solution) was added, and the mixture was stirred for 30 minutes. The organic layer was separated, washed with 1% aqueous sodium carbonate (2×300 mL). Citric acid (10% aqueous solution) was added to aid in the separation. The organic layer was then washed twice with 10% aqueous citric acid, and the combined aqueous washings were extracted with chloroform (3×150 mL). The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was dried overnight under vacuum to provide 28.49 g of tert-butyl 5-oxido-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate as a brown solid.

Provenance & Evidence