Tetrahydrofuran → [2-(4-Cyclobutylpiperidin-4yl-oxy)-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl]-cyclopropyl-methanone

Participants

Reaction Steps

1-Cyclobutyl-piperidin-4-ol (0.04 grams, 0.26 mmol) in tetrahydrofuran (3 mL) was treated with cooled and stirred suspension of sodium hydride (0.021 grams, 0.51 mmol) in tetrahydrofuran (8 mL) slowly over the period of 5 minutes and the reaction mixture was stirred for 2 hours at room temperature. A solution of (2-Bromo-4,5,7,8-tetrahydro-thiazolo[5,4-d]azepin-6-yl)-cyclopropyl-methanone (0.053 grams, 0.17 mmol, obtained in above step) in tetrahydrofuran (3 mL) was added drop wise over a period of 5 minutes and refluxed for 15 hours. Reaction mass was quenched onto ice cold water and the product was extracted with ethyl acetate (3×10 mL). The combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. Organic volatiles were evaporated under vacuum. The residue obtained was purified by flash chromatography (methanol/chloroform 3/97) to obtain the title compound (0.05 grams).

Provenance & Evidence