AMINO DIOL BASED ASYMMETRIC SYNTHESES OF A FUSED BENZAZEPINE AS A SELECTIVE D1 DOPAMINE-RECEPTOR

A six-step practical synthesis of o-7-methyl-5H-benzo[d]naphtho-[2,1-b ]azepin-12-ol, a selective D1 dopamine receptor, is developed starting from (1S,2S)-phenyl-2-amino-1,3-propanediol. An acid-promoted stereo- and regioselective cyclization of the benzazepine ring was established . Three double reactions in which two functional groups are transforme d in a single step were developed, These include the double hydrolysis , the double reduction, and the cyclization and demethylation. The use of practical and economical reagents reduced the cost significantly.