Syntheses related to northebaine. Part II. Derivatives of nororipavine and 8,14-dihydronororipavine

Abstract

Some N-substituted 8,14-dihydronororipavines have been synthesised by O-methylation of N-acyl or N-alkenyl O(N′N′-diethylcarbamyl)dihydronormorphinones followed by lithium aluminium hydride reduction of the intermediate enol ether-carbamate esters. Some nicotinoyl esters are described.

N-Cyclopropylcarbonyl-O(N′N′-diethylcarbamyl)-8,14-dihydronororipavine on treatment with methyl hypobromite followed successively by dehydrobromination, lithium aluminium hydride reduction, and finally mild treatment with acid,gave N-cyclopropylmethylnororipavine.