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US 8,013,157 B2Granted
Synthesis of unsaturated piperidines from piperidones with a silyl reagent
AssigneeJanssen Pharmaceutica NV
InventorsNeelakandha S. Mani, Christie Morrill
Life of this patent
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Abstract
Syntheses of unsaturated piperidines from piperidones through a silyl piperidine reagent via the Shapiro reaction and palladium-catalyzed cross-coupling reactions with organo halides.
Claims29
A compound of formula (I)
- wherein
- R1 and R2 are independently chosen from the group of alkyl, and alkyl substituted with at least one of halo, hydroxy, alkoxy, —COOH, and —COOAlkyl;
- R3 is chosen from the group of H, Ar, heteroaryl, fluoro, hydroxyl, —OR1, and —O—R5;
- R5 is
- and
- R4 is chosen from the group of Ar, cycloalkyl, heterocycloalkyl, and heteroaryl, where R3 and R4 are independently optionally substituted with at least one of halo, hydroxy, alkoxy, —COOH, and —COOAlkyl;
- or a salt thereof.
4 more elements
A process for the preparation of an unsaturated piperidine, comprising making a compound of formula (I) from a hydrazone, and said compound of formula (I) is
- wherein
- R1 and R2 are independently chosen from the group of alkyl, and alkyl substituted with at least one of halo, hydroxy, alkoxy, —COOH, and —COOAlkyl;
- R3 is chosen from the group of H, Ar, heteroaryl, fluoro, hydroxyl, —OR1, and —O—R5;
- R5 is
- and
- R4 is chosen from the group of Ar, cycloalkyl, heterocycloalkyl, and heteroaryl, where R3 and R4 are independently optionally substituted with at least one of halo, hydroxy, alkoxy, —COOH, and —COOAlkyl;
- and salts thereof.
4 more elements
Dependencies are inferred from the claim text.