Citric Acid → 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylate (110 mg, 0.24 mmol) in methanol (10 mL) was added aqueous sodium hydroxide solution (1 N, 2 mL, 2 mmol) dropwise followed by water (2 mL). The reaction mixture was stirred at RT for 15 min before neutralized with hydrochloric acid solution (6 N, 0.3 mL) and aqueous 10% citric acid solution. The mixture was concentrated under reduced pressure to remove methanol. The solid was filtered, washed with water, and dried to give 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylic acid.

Provenance & Evidence