Process for N-dealkylation of tertiary amines
AssigneeRhodes Technologies
InventorsJoshua Robert Giguere, Helge Alfred Reisch, Sergio Sandoval, Jake Larry Stymiest
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Abstract
The present disclosure provides improved methods for N-dealkylation of tertiary amines, including methods for N-demethylation of alkaloids and opioids, in which the dealkylation reaction is carried out in a solvent comprising a tertiary alcohol. The present disclosure also provides improved processes for preparing semi-synthetic opioids that incorporate the disclosed methods for N-dealkylation of tertiary amines.
Claims37
A composition prepared by combining a compound of formula (12)
- a compound of formula (2)
- and
- a tertiary alcohol;
- wherein
- the bond is a single bond or a double bond;
- R9 is selected from the group consisting of —OH, —H, and —OR15;
- R19 is selected from the group consisting of —H, —OH, —CH3, and —OR15;
- R15 is an oxygen protecting group;
- R4 is selected from the group consisting of —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, aryl, and heteroaryl, each being unsubstituted or substituted with 1, 2, 3, 4, or 5 independently-selected R5 groups;
- each R5 is independently selected from the group consisting of —OH, —Cl, —Br, —I, —NH2, —CN, —O—(C1-C6) alkyl, and phenyl;
- and
- X is selected from the group consisting of —Cl, —Br, —I, mesylate, and tosylate.
A composition prepared by combining a compound of formula (16)
- a compound of formula (2)
- and
- a tertiary alcohol;
- wherein
- the bond is a single bond or a double bond;
- R9 is selected from the group consisting of —OH, —H, and —OR15;
- R19 is selected from the group consisting of —H, —OH, —CH3, and —OR15;
- R15 is an oxygen protecting group;
- R4 is selected from the group consisting of —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, aryl, and heteroaryl, each being unsubstituted or substituted with 1, 2, 3, 4, or 5 independently-selected R5 groups;
- each R5 is independently selected from the group consisting of —OH, —CI, —Br, —I, —NH2, —CN, —O—(C1-C6) alkyl, and phenyl;
- and
- X is selected from the group consisting of —Cl, —Br, —I, mesylate, and tosylate.
A composition comprising a tertiary alcohol and a compound of formula (2)
- wherein
- R4 is selected from the group consisting of —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, aryl, and heteroaryl, each being unsubstituted or substituted with 1, 2, 3, 4, or 5 independently-selected R5 groups;
- each R5 is independently selected from the group consisting of —OH, —Cl, —Br, —I, —NH2, —CN, —O—(C1-C6) alkyl, and phenyl;
- and
- X is selected from the group consisting of —Cl, —Br, —I, mesylate, and tosylate.
Dependencies are inferred from the claim text.