Hydrochloric Acid → 1-Azabicyclo[3.2.2]non-5-yl(5-phenyl-1,3-thiazol-4-yl)carbamate

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Reaction Steps

To a solution of 5-phenyl-1,3-thiazole-4-carboxylic acid (385 mg) in toluene (8 mL) was added TEA (285 μL) at room temperature. To the reaction mixture was added dropwise DPPA (404 μL), followed by stirring at the same temperature for 40 minutes. In addition, after stirring at 90° C. for 5 minutes, a mixture of 1-azabicyclo[3.2.2]nonan-5-ol (313 mg) and DMF (3 mL) was added thereto, followed by stirring at 110° C. for 1 hour. The reaction mixture was cooled to room temperature, followed by addition with 1 M hydrochloric acid for acidification, and extraction with EtOAc. The aqueous layer was alkalified with addition of a 1 M aqueous NaOH solution, and extracted with CHCl3. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, CHCl3:MeOH:aqueous ammonia) to obtain a yellow amorphous fluorescent substance. To this was added EtOAc, and the resulting solid was collected by filtration, and washed with EtOAc to obtain 1-azabicyclo[3.2.2]non-5-yl(5-phenyl-1,3-thiazol-4-yl)carbamate (238 mg) as a colorless powder.

Provenance & Evidence