Chemical methods
AssigneeGlaxoWellcome Australia Ltd.
InventorsPeter Scammells, Nicholas Gathergood, Justin Ripper
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Abstract
This invention relates to a method for N-demethylating an N-methyl morphinane comprising the steps of: (i) treating said N-methyl morphinane with an oxidizing agent to form the N-oxide morphinane; and (ii) treating said N-oxide morphinane with a reducing agent. This invention also relates to a method for oxidizing a Δ7-morphinane compound to a Δ6, Δ8-morphinane compound, comprising the steps of treating said Δ7-morphinane with γ-MnO2 for a time and under conditions sufficient to oxidize said Δ7-morphinane, and treating the γ-MnO2 with glycol or a derivative thereof, and/or an inorganic salt.
Claims22
A method for N-demethylating an N-methyl morphinane selected from compounds of formulae (i), (ii) and (iii):
- wherein
- R and R1 are independently a hydrogen, methyl or ethyl group,
- R2 and R3 together form a carbonyl or a ═CH2 group, R4 is hydrogen and R5 is hydrogen or a hydroxy group and
- is an optional double bond;
- or
- R2 is methoxy or hydroxy, R3 and R5 together form an ethylene or ethenyl group and
- R4 is a hydroxy or keto-substituted straight or branched C1-6 alkyl group;
- or a
- protected derivative thereof,
- comprising the steps of:
- (i) treating said N-methyl morphinane with an oxidising agent to form the N-oxide morphinane;
- and
- (ii) treating said N-oxide morphinane with a reducing agent.
A method for oxidising a protected Δ7-morphinane compound to a Δ6, Δ8-morphinane compound, wherein the Δ7-morphinane compound is a compound of formula (8):
- wherein R and R1 are selected from independently hydrogen, C1-6 alkyl, C(O)C1-6 alkyl, benzyl, phenyl or a hydroxy protecting group and R′ is hydrogen, a nitrogen protecting group, C1-6 alkyl, C1-6 alkenyl, or C1-6 alkynyl, comprising the steps of treating said Δ7-morphinane with γ-MnO2 for a time and under conditions sufficient to oxidise said Δ7-morphinane, and treating the γ-MnO2 with glycol or a derivative thereof, and/or an inorganic salt.
Dependencies are inferred from the claim text.