Apomorphinans from Isoquinolines: Grewe Cyclization of 1-(2-Hydroxybenzyl)-N-methyloctahydroisoquinoline and its O-Methyl Ether

Article abstract of DOI:10.1002/hlca.19830660807

Wolff-Kishner reduction of the optically active ketomorphinan 5 afforded the optically active morphinan 6 differing chromatographically and spectroscopically from the material obtained in a Grewe-cyclization of the isoquinoline 1.A single crystal X-ray analysis of a hydrobromide salt of a phenolic amine obtained from 1 and 2 with refluxing hydrobromic acid showed this compound to be the N-methylapomorphinan 4.