Synthesis of 3,6-dialkyl-5,6-dihydro-4-hydroxy-pyran-2-one

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

Reexamination Certificate

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C560S188000

Reexamination Certificate

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06858749

ABSTRACT:
The present invention relates to a novel process for producing a δ-lactone of the formula:using an acyl halide of the formula:wherein R1, R2R3and X are described herein, as well as novel intermediates. In particular, the present invention relates to a process for enantioselectively producing the (R)-δ-lactone.

REFERENCES:
patent: 4962230 (1990-10-01), Takaya et al.
patent: 4962242 (1990-10-01), Yamada et al.
patent: 5066815 (1991-11-01), Sayo et al.
patent: 5144057 (1992-09-01), Eyer
patent: 5194671 (1993-03-01), Meier
patent: 5245056 (1993-09-01), Karpf et al.
patent: 5274143 (1993-12-01), Ramig et al.
patent: 5399720 (1995-03-01), Karpf et al.
patent: 5420305 (1995-05-01), Ramig et al.
patent: 5945559 (1999-08-01), Sotoguchi et al.
Landl, John J. et al., “A New Route to β-Keto-δ-lactones: Practical Preparation of (R)-3-Hexyl-5, 6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one, a Key Intermediate in Asymmetric Synthesis of Tetrahydrolipstatin,” Tetrahedron Letters, vol. 34, No. 2, pp. 277-280 (1993).
Miura, Katsukiyo et al., “Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers and Ketene Silyl Acetals with Perfluoroalkyl Iodides,” Bull. Chem. Soc. Jpn., vol. 64, No. 5, pp. 1542-1553 (1991).
Umemoto, Teruo et al., “1H,1H-Perfluoroalkylation of Enol Silyl Ethers with (1H,1H-Perfluoroalkyl)-phenyliodonium Triflates. A New Method for the Preparation of β- and δ-Trifluoromethyl Carbonyl Compounds and Their Higher Perfluoroalkyl Homologues),” Bull. Chem. Soc. Jpn., vol. 60, pp. 3823-3825 (1987).
Sugimoto, Jiro et al., “Triethylborane Induced Radical Reaction of Ketene Silyl Acetals with Polyhalomethanes. Synthesis of 3,3-Dihalo- and 3-Haloacrylates,” The Chemical Society of Japan, Chemistry Letters, pp. 1319-1322 (1991).
Miura, Katsukiyo et al., “Triethylborane Induced Radical Reaction of Keten Silyl Acetals with Polyhalomethanes,” Bull. Chem. Soc. Jpn. vol. 65, pp. 1513-1521 (1992).
Shono, Tatsuya et al., “Electroorganic Chemistry. 82. βAmino Acid Esters for α-Methoxycarbamates and Ketene Silyl Acetals; Cyclization to β-Lactams,” J. Org. Chem. vol. 49, pp. 1056-1059 (1984).
Purrington, Suzanne T. et al., “Preparation of α-Fluoro Carboxylic Acids and Derivatives,” J. Org. Chem., vol. 55, pp. 3423-3424 (1990).
Clay, Ronald J. et al., “A Safe, Economical Method for the Preparation of β-Oxo Esters,” Synthesis, pp. 290-292 (1993).
Rathke, Michael W. et al., “Procedures for the Acylation of Diethyl Malonate and Ethyl Acetoacetate with Acid Chlorides Using Tertiary Amine Bases and Magnesium Chloride,” J. Org. Chem, vol. 50, pp. 2622-2624 (1985).
Trost, Barry M. et al., “Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry,” vol. 6, Pergamon Press, pp. 301-319.
Pommier, Agnes et al., “An Asymmetric Synthesis of (-)-Tetrahydrolipstatin,” Synthesis, pp. 1294-1295 (1994).
Schmid, R. et al., “Asymmetric hydrogenation in process research of pharmaceuticals, vitamins and fine chemicals,” Chiral Europe (1994).
Case-Green, Stephen C. et al., “Asymmetric Synthesis of (-)-Tetrahydrolipstatin,” Synlett, pp. 781-782, Nov. 1991.
Kitamura, Masato et al., “Asymmetric Synthesis of β-Hydroxy Sulfonic Acids by BINAP/Ru-Catalyzed Hydrogenation,” Tetrahedron, vol. 55, pp. 8769-8785 (1999).
Pye, Philip J. et al., “[2.2]PHANEPHOS-Ruthenium(II) Complexes: Highly Active Asymmetric Catalysts for the Hydrogenation of β-Ketoesters,” Tetrahedron Letters, vol. 39, pp. 4441-4444 (1998).

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