Process for obtaining enantiomers of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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06979742

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 more generally for thyenylazolylalcoxyethanamines and their enantiomers. The process involves the asymmetric reduction of a prochiral ketone in the presence of a chiral ruthenium (II) catalyst system comprising at least a bidentate phosphorous-containing ligand and a diamine ligand to yield chiral alcohols. The chiral alcohols are further O-alkylated to yield corresponding pharmaceutically active ethanamines.

REFERENCES:
patent: 6743921 (2004-06-01), Tucker et al.
patent: 0 289 380 (1994-12-01), None
patent: WO 99/02500 (1999-01-01), None
patent: WO 99/52525 (1999-10-01), None
patent: WO 2004/011452 (2004-02-01), None
Burk, Mark J., et al.,A Catalyst for Efficient and Highly Enantioselective Hydrogenation of Aromatic, Heteroaromatic, and α,β-Unsaturated Ketones, Org. Lett., vol. 2, (2000) 4173-4176.
Cao, Ping, et al.,Ru-BICP-Catalyzed Asymmetric Hydrogenation of Aromatic Ketones, J. Org. Chem.vol. 64, (1999) 2127-2129.
Chen, Cheng-yi, et al.,Highly Enantioselective Hydrogenation of Aromatic-Heteroaromatic Ketones, Org. Lett., vol. 5, (2003) 5039-5042.
Noyori, Ryoji, et al.,Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo-and Stereoselective Hydrogenation of Ketones, Angew. Chem. Int. Ed., vol. 40, (2001) 40-73.
Wu, Jing, et al.,Air-Stable Catalysts for Highly Efficient and Enantioselective Hydrogenation of Aromatic Ketones, J. Org. Chem.vol. 67, (2002) 7908-7910.

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