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US 9,073,934 B2Granted
Method for the N-demethylation of N-methyl heterocycles
AssigneeMonash University
InventorsPeter John Scammells, Gaik Orbell
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Abstract
The present invention provides methods of N-demethylating, N-methylated heterocycles and N-methyl, N-oxide heterocycles using a transition metal with an oxidation state of zero, ferrocene or substituted derivatives thereof, or Cr3+. N-demethylated heterocycles prepared by the methods of the present invention are also provided.
Claims20
A method of N-demethylating an N-methylated heterocycle, said method comprising the steps of:
- (i) oxidizing an N-methylated heterocycle to form an N-methyl, N-oxide heterocycle, and
- (ii) exposing the N-methyl, N-oxide heterocycle to a transition metal with an oxidation state of zero;
- wherein the N-methylated heterocycle is an N-methyl morphine alkaloid or an N-methyl tropane alkaloid.
A method of preparing an N-demethylated heterocycle from an N-methyl, N-oxide heterocycle, the method comprising:
- (i) providing an N-methyl, N-oxide heterocycle formed from an N-methylated heterocycle;
- and
- (ii) exposing the N-methyl, N-oxide heterocycle to a transition metal with an oxidation state of zero;
- wherein the N-methylated heterocycle is an N-methyl morphine alkaloid or an N-methyl tropane alkaloid.
1 more element
Dependencies are inferred from the claim text.