Sodium Hydroxide → α-(1,1-Dimethylethoxy)-5,6,7,8-tetrahydro-2-methyl-4-(6-methyl-3-pyridinyl)[1]benzothieno[2,3-b]pyridine-3-acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-[2-methyl-4-(6-methylpyridin-3-yl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate (0.035 g; 0.080 mmol) in methanol (1 mL) was added a solution of sodium hydroxide 10 N (0.100 mL; 1 mmol) and the mixture was heated at 60° C. for 18 h. The volatiles were removed under reduced pressure and the residue was dissolved in water. The mixture was then acidified by adding 1N HCl until a precipitate was formed. The solid was filtered, washed with water and dried under reduced pressure. The crude product was suspended in a mixture of acetonitrile and methanol, filtered, washed with acetonitrile and dried under reduced pressure to furnish 0.007 g (20%) of the title compound as a white solid.

Provenance & Evidence