Acetic Acid → HCID 131710910, compound

Participants

Reaction Conditions

Reaction Steps

Finely-ground trans-8-[(6-fluoro-1,2,3,4-tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]-decan-4-one (3g, see example 116) is added in small portions to a rapidly stirred acid solution comprising 20 ml acetic acid containing 20% v/v sulfuric acid maintained at 25° C. The resulting light-brown solution is stirred overnight at room temperature under nitrogen. The dehydration mixture is then gently warmed on a steam bath for 10 minutes. The warm solution is poured into ice-water (400 ml) and the resulting suspension basified with solid sodium bicarbonate. Extraction with chloroform yields a tan solid (1.9 g. 66%) containing small amounts of three impurities detected by TLC analysis. High pressure liquid chromatography (HPLC) of this material on silica gel with ethyl acetate gives 1.5 g of the free base of the title compound as colorless prisms, melting point 186°-187° C.

Provenance & Evidence