Process for obtaining enantiomers of thienylazolylalcoxyethanamines
AssigneeLaboratories Del Dr. Esteve, S.A.
InventorsAntoni Jover, Helmut Buschmann, Stefan Dahmen, Matthias Lormann
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Abstract
A process is described for the preparation of a precursor alcohol of (±)-2-[thienyl(1-methyl-1H-pyrazol-5-yl)methoxy]-N,N-dimethyletanamine and in general for thienylazolylalcoxyethanamines and their enantiomers. The process involves asymmetric addition of a metalated thienyl reagent to a pyrazolcarbaldehyde in the presence of a chiral ligand to yield chiral alcohols. The chiral alcohols are further O-alkylated to yield the corresponding pharmaceutically active thienylazolylalcoxyethanamines.
Claims20
A process for the preparation of an enantiomerically enriched compound of formula (II):
- wherein:
- R1 and R2 are independently selected from hydrogen, halogen, lower alkyl and aryl;
- which comprises an enantioselective addition reaction to a methylpyrazolcarbaldehyde compound of formula (IV):
- with a thienyl zinc reagent optionally substituted on the thienyl ring, in the presence of a chiral ligand.
A process for the preparation of a precursor alcohol of (±)-2-[thienyl(1-methyl-1H-pyrazol-5-yl)methoxy]-N,N-dimethyletanamine, comprising asymmetric addition of a metalated thienyl reagent to a pyrazolcarbaldehyde in the presence of a chiral ligand to yield said precursor alcohol.
A process for preparation of thienylazolylalcoxyethanamine, comprising asymmetric addition of a metalated thienyl reagent to a pyrazolcarbaldehyde in the presence of a chiral ligand to yield chiral alcohol, and O-alkylating said chiral alcohol to yield said thienylazolylalcoxyethanamine.
Dependencies are inferred from the claim text.