Citric Acid → ethyl 5-[({6-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]pyrazine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

1.00 g of tert-butyl (6-hydroxy-2,3-dihydro-1H-inden-5-yl)carbamate was dissolved in 10.0 mL of DMF, and 1.08 g of ethyl 5-(bromomethyl)pyrazine-2-carboxylate and 721 mg of potassium carbonate were added thereto, followed by stirring at 60° C. for 1 hour. The reaction liquid was poured into a 5% w/v aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with a 5% w/v aqueous citric acid solution, water, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to obtain 690 mg of ethyl 5-[({6-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl}oxy)methyl]pyrazine-2-carboxylate.

Provenance & Evidence