Synthesis and stereochemistry of 1,2,3,4-tetrahydro-6-methoxy-2-methyl-1-phenylisoquinoline and related compounds

Abstract

The absolute configurations of (1R,4R)-1,2,3,4-tetrahydro-4-hydroxy-6-methoxy-2-methyl-1-phenylisoquinoline (XIa) and its epimer, which were synthesised by cyclisation of D-(+)-2-amino-1-(3-hydroxyphenyl)ethanol with benzaldehyde, followed by Eschweiler-Clarke methylation, were determined by their n.m.r. spectra. The relationship between the absolute configuration of (1R)-1,2,3,4-tetrahydro-6-methoxy-2-methyl-1-phenylisoquinoline and its o.r.d. curve was also revealed.