Polonovski-Type N-Demethylation of N-Methyl Alkaloids Using Substituted Ferrocene Redox Catalysts

Gaik B. Kok, Peter J. Scammells*

*Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, Victoria, 3052, Australia, Email: peter.scammellsmonash.edu

G. B. Kok, P. J. Scammels, Synthesis, 2012, 44, 2587-2594.

DOI: 10.1055/s-0032-1316590

---

Abstract

The bifunctional ferrocene FcCH₂CO₂H, with electron donor and acceptor moieties in the same molecule, has been shown to be advantageous for use as a catalyst in the N-demethylation of a number of tertiary N-methylamines such as codeine, thebaine, and oripavine. These substrates are readily N-demethylated under mild conditions, employing sub-stoichiometric amounts of the substituted ferrocene at ambient temperature.

see article for more examples

---

---

New Methodology for the N-Demethylation of Opiate Alkaloids

Z. Dong, P. J. Scammels, J. Org. Chem., 2007, 72, 9881-9885.

---

Key Words

N-demethylation, N-Dealkylation, Polonovski reaction, substituted ferrocene, alkaloid

---

ID: J66-Y2012-2630