2,4-Dimethyl-1,3-thiazole-5-carbaldehyde → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2,4-dimethyl-1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

Participants

Reaction Steps

In 1,2-dichloroethane (21 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-benzazepine-4-carboxylate (0.70 g). To the solution were added 2,4-dimethyl-1,3-thiazole-5-carbaldehyde (0.62 g) and sodium triacetoxyborohydride (1.5 g), and the mixture was stirred at room temperature for 36 hours. After stirred at 60° C. for 12 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=1/1) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2,4-dimethyl-1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.26 g).

Provenance & Evidence