SYNTHESIS OF ANISODAMINE ANALOGS

Twelve anisodamine analogs (Ⅰ-Ⅻ) were synthesized by esterification of 6β-hydroxy, 6β-methoxy and 6,7β-dimethoxy tropanol with various acid chlorides most of which contain neurotropic functional groups such as halides, epoxide etc. Physical data of compounds Ⅰ-Ⅻ are listed in table 1.Besides, three △⁶-tropenol esters (ⅩⅢ-ⅩⅤ) were prepared by the following process.6β-Tosyloxy-3α-acetoxy tropane was refluxed in diglyme for several hours. The 3α-acetoxy-△⁶-tropene so obtained was then hydrolysed to give △⁶-tropen-3α-ol. Finally, △⁶-tropenol was esterified respectively with tropoyl chloride by heating without solvent, with benzoyl chloride in refluxing chloroform, and with atropoyl chloride in the presence of pyridine (use of pyridine being mandatory) to produce the corresponding esters ⅩⅢ,ⅥⅤ and ⅩⅤ.IR, NMR and MS of compounds Ⅰ-ⅩⅤ were discussed.