Methods of o-demethylation and n-deprotection
AssigneeThe United States as represented by the Department of Health and Human Services
InventorsAndrew Coop, Kenner C. Rice
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Abstract
The present invention provides a method for N-deprotecting an opioid compound, a method for N-deprotecting and O-demethylating an opioid compound, a method for O-demethylating an opioid compound, and a method for O-demethylating a nonpeptidic delta agonist compound or an opioid compound having a tertiary amide with no significant reaction at amide groups.
Claims18
A method for the aromatic O-demethylation of an opioid compound comprising admixing said opioid compound and a hydride reagent selected from the group consisting of lithium tri-sec-butylborohydride, lithium trisiamylborohydride and lithium triethylborohydride to produce an O-demethylated opioid compound, wherein the yield of the O-demethylated opioid compound is at least 23%.
A direct method for the preparation of oripavine from thebaine comprising admixing thebaine with lithium tri-sec-butylborohydride.
A method for the aromatic O-demethylation of an opioid compound comprising admixing said opioid compound with a hydride reagent selected from the group consisting of lithium tri-sec-butylborohydride, lithium trisiamylborohydride and lithium triethylborohydride, and refluxing the mixture, to produce an O-demethylation opioid compound, wherein the yield of the O-demethylated opioid compound is at least 23%.
A method for the aromatic O-demethylation of an opioid compound having at least one amide group with minimal or no reaction at the amide group comprising admixing said opioid compound and a hydride reagent selected from the group consisting of lithium tri-sec-butylborohydride and lithium trisiamylborohydride.
A method for the aromatic O-demethylation of an opioid compound comprising admixing at a temperature of about 20° C. to about 70° C. said opioid compound and a hydride reagent selected from the group consisting of lithium tri-sec-butylborohydride, lithium trisiamylborohydride and lithium triethylborohydride to produce an O-demethylated opioid compound.
A method for the aromatic O-demethylation of an opioid compound comprising, at a temperature of about 20° C. to about 70° C., admixing said opioid compound with a hydride reagent selected from the group consisting of lithium tri-sec-butylborohydride, lithium trisiamylborohydride and lithium triethylborohydride, and refluxing the mixture, to produce an O-demethylated opioid compound.
Dependencies are inferred from the claim text.