Continuous process for the enantioselective catalytic...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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Reexamination Certificate

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07057064

ABSTRACT:
The present invention relates to a continuous process for the enantioselective catalytic hydrogenation of β-ketoesters comprising providing a catalytic hydrogenation zone and maintaining it under conditions of temperature and pressure effective for the catalytic hydrogenation of β-ketoesters; continuously supplying to the catalytic hydrogenation zone a substrate comprising a β-ketoester to be hydrogenated, a catalyst effective for enantioselective hydrogenation of the β-ketoester and hydrogen; contacting the substrate, the catalyst and the hydrogen in the hydrogenation zone for a residence time effective for at least partial enantioselective catalytic hydrogenation of the β-ketoester; (d) continuously withdrawing from the hydrogenation zone a reaction product mixture comprising enantioselectively hydrogenated β-ketoester, unreacted β-ketoester, catalyst and hydrogen; (e) supplying the reaction product mixture to a separation zone and separating at least some of the enantioselectively hydrogenated β-ketoester from the reaction product mixture; (f) withdrawing the separated enantioselectively hydrogenated β-ketoester as product; and (g) optionally supplying at least part of the remaining material from the separation zone to the hydrogenation zone.

REFERENCES:
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PCT International Search Report, International Application No. PCT/ GB 03/ 02192, Applicant: Phoenix Chemicals Limited.
Kitamura, M., et al.,A Practical Asymmetric Synthesis Of Carnitine, Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, vol. 29, No. 13, 1988, pp. 1555-1556, XP001033752.
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International Preliminary Examination Report, International application No. PCT/GB 03/02192, Applicant: Phoenix Chemicals Limited et al.
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Kitamura, M., et al.,Convenient Preparation Of Binap-Ruthenium(II)Complexes Catalyzing Asymmetric Hydrogenation Of Functionalized Ketones, Tetrahedron Letters, vol. 32, pp. 4163-4166, 1991, Pergamon Press plc.
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Pavlov, V.A.., et al.,Enantioselective hydrogenation of β-keto esters catalyzed by chiral binaphthylbisphosine ruthenium complexes, Russian Chemical Bulletin, vol. 49, No. 4, Apr., 2000.
Ager, David,Reductions of 1,3-dicarbonyl systems with ruthenium-biarylbisphosphine catalysts, Tetrahedron: Asymmetry, vol. 8, No. 20, pp. 3327-3355, 1997 Elsevier Science Ltd.

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