E. Warawa, N. J. Mueller
1975
Citations
0
Influential Citations
10
Citations
Journal
Journal of medicinal chemistry
Abstract
The 1,4 addition of p-chlorophenylmagnesium bromide to 2-benzylidene-3-quinuclidinone gave 2-(4-chlorobenzhydryl)-3-quinuclidinone as two diastereoisomers. Selective reduction of this ketone with aluminum isopropoxide gave the two cis-2-(4-chlorobenzhydryl)-3-quinuclidinols, which differ only in the configuration of the benzhydryl group, designated alpha and beta in order of their elution on chromatography. Reduction with NaBH4 gave a mixture of four isomeric alcohols, of which the two cis isomers were selectively oxidized. The two trans-2-(4-chlorobenzhydryl)-3-quinuclidinols were chromatographically separated and desingated alpha and beta in order of elution. Only the beta-cis and beta-trans alcohols showed CNS stimulant properties. The beta-cis isomer was shown to be related both qualitatively and quantitatively more to methylphenidate (Ritalin) than to d-amphetamine.