O-Methylation of hydroxy-aporphine derivs. - using e.g phenyl tri:methyl ammonium hydroxide to form (n)-propyl 1,2,9,10-tetra:methoxy and 1-hydroxy-2,9,10 tri:methoxy (n)-noraporphine

摘要

In the O-methylation of hydroxy-aporphines of formula (I) the phenolic hydroxyl groups are O-methylated with a phenyl-trimethyl-ammonium deriv. of formula (II) in an inert solvent and the prod. isolated and if desired converted to its salt. In the formulae, >=1 of R1-R7 is hydroxy whilst the other groups are H or substits. which are inert under the reaction conditions, R8 is lower alkyl (=5C pref. =3C) and X is hydroxy or lower alkoxy. N-n-propyl-1,2,9,10-tetramethoxy-N-noraporphine and (I)-1-hydroxy-N-2-propyl-2,9,10-trimethoxy-N-noraporphine and their salts are new. (I) are pharmaceuticals and intermediates e.g 1,2,10-trimethoxy-9-(3',4'-dimethoxy)-phenoxy-aporphine is a precursor for hernandaline a key cpd. in the synthesis of the anti-tumour agent, thalicarpine.