Thionyl Chloride → HCID 86692532, compound

Participants

Reaction Steps

To a solution of 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxyazepane-1-carboxylic acid tert-butyl ester (1.90 g) in pyridine (20 ml) was added thionyl chloride (1.47 g) under ice-cooling, and stirred at the same temperature for 1 hour. After completion of the reaction, saturated sodium bicarbonate water was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give a mixture (1.02 g) of 4-(5-bromo-3-methylpyridin-2-yl)-2,3,6,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester and 4-(5-bromo-3-methylpyridin-2-yl)-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester as a colorless clear oil.

Provenance & Evidence