Pharmacology N-dealkylation of Morphinans and Related Opioids in Good Yields using Mild Conditions and Non-Toxic Reagents (non-classical Polonovski)

[3DQSAR]

https://sciforum.net/manuscripts/1516/original.pdf

If you follow the references you finally end up with 'non-classical Polonoski Reactions'.

Note that the N-cyclopropylmethyl homologue produces similar yields so naltrexone-->noroxymorphone is facile.

I feel that those who understand the possibilities this work possible make it an interesting read. The 14-hydroxy morphinans appear to follow the QSAR of homologues with the 4.5-epoxy bridge so one would imagine that the N-phenylethyl or better. the N-(2-(2-furanylethyl)) products will be QUITE potent (480-640x M is my best guess).

 

[3DQSAR]

Sci-Hub | Secondary Amines from the lron(II) Ion-Catalyzed Reaction of Amine Oxides: A General Method for the Dealkylation of Tertiary Amines. Synthesis, 1985(08), 770–773 | 10.1055/s-1985-31342

Title
Secondary Amines from the Iron(II) Ion-Catalyzed Reaction of Amine Oxides: A General Method for the Dealkylation of Tertiary Amines.

Note the above is the key reference in the paper I posted. It's worth understanding that the phenol has to be protected because the iron salt forms a complex with it. BUT it offers a convenient and quite general way to N-dealkylate a large number of compounds. While the nor conpounds may not be very active in their own rights, the task of N-alkylation is a much simpler problem to solve.