New methodology for the N-demethylation of opiate alkaloids

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N-Demethylation is a key step in the preparation of a number of semisynthetic opiate pharmaceuticals. Herein we report a high-yielding, catalytic procedure for the N-demethylation of opiates which has a number of advantages over existing methods. For example, tetrasodium 5,10,15,20-tetra(4-sulfophenyl)porphyrinatoiron(II) (0.3 molar equiv) effected the transformation of codeine methyl ether to the corresponding N-nor analogue in 91 yield. The catalyst was readily removed and recycled.
Original languageEnglish
Pages (from-to)9881 - 9885
Number of pages5
JournalThe Journal of Organic Chemistry
Issue number26
Publication statusPublished - 2007

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