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.
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.
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Z. Dong, P. J. Scammels, J. Org. Chem., 2007, 72, 9881-9885.
N-demethylation, N-Dealkylation, Polonovski reaction, substituted ferrocene, alkaloid