Acetic Acid → Quilostigmine

Participants

Reaction Steps

To the ethyl acetate solution (which contained (-)-eseroline) was added, under N2, 13.17 g (1.0 equiv) of 1,1'-carbonyldiimidazole, as a solid, in several portions. This was followed by the addition of 13.16 g (3.0 equiv) of glacial acetic acid and 10.81 g (1.07 equiv) of 1,2,3,4-tetrahydroisoquinoline in 20 mL of ethyl acetate. After stirring overnight, the reaction mixture was extracted with 200 mL of water. The ethyl acetate solution was further extracted twice with 100 mL of 0.5N sodium hydroxide solution, and 100 mL of water. After drying over anhydrous sodium sulfate, the ethyl acetate solution was concentrated under reduced pressure to give 24.66 g (80.5%) of crude product.

Provenance & Evidence