New methodology for the N-demethylation of opiate alkaloids.
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.
Dong
Zemin
Z
Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville, Victoria 3052, Australia.
Scammells
Peter J
PJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D058085:Iron Compounds / Q000737:chemistry; D008665:Metalloporphyrins / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D011166:Porphyrins / Q000737:chemistry; D013237:Stereoisomerism
C527458:5,10,15,20-tetrakis(4-sulfophenyl)porphyrinatoiron(II); D000470:Alkaloids; D001557:Benzenesulfonates; D058085:Iron Compounds; D008665:Metalloporphyrins; D011166:Porphyrins