Process for the synthesis of 1,3-diols

Details Process for the synthesis of 1,3-diols Process for the synthesis of 1,3-diols

2007-06-19

2007-06-19

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S022000, C549S039000, C549S264000, C549S333000

Reexamination Certificate

active

11119151

ABSTRACT:
An improved process for the preparation of cis-1,3-diols is described where a beta hydroxy ketone is treated with a trialkylborane or dialkylalkoxyborane or a mixture of a trialkylborane and a dialkylalkoxyborane followed by recovery and reuse of the alkylborane species to convert additional beta hydroxy ketone to the cis-1,3-diol.

REFERENCES:
patent: 4208354 (1980-06-01), Demosthene et al.
patent: 4645854 (1987-02-01), Verhoeven et al.
patent: 4897490 (1990-01-01), Sit et al.
patent: 4898949 (1990-02-01), Wright et al.
patent: 4970313 (1990-11-01), Wess et al.
patent: 5001144 (1991-03-01), Regan et al.
patent: 5003080 (1991-03-01), Butler et al.
patent: 5082859 (1992-01-01), Festal et al.
patent: 5145857 (1992-09-01), Fey et al.
patent: 5155251 (1992-10-01), Butler et al.
patent: 5273995 (1993-12-01), Roth et al.
patent: 5298627 (1994-03-01), Butler et al.
patent: 5354772 (1994-10-01), Kathawala
patent: 5401746 (1995-03-01), Angerbauer et al.
patent: 0 017 175 (1980-03-01), None
patent: 0 002 142 (1982-08-01), None
patent: 0 453 298 (1995-12-01), None
patent: 0742209 (1996-11-01), None
Sato, M., et al. “Aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines with chiral aldehydes: Enantioselective synthesis of 1,3,-dioxin-4-ones having a 2,3-dihydroxylated alkyl group at the 6-position”Tetrahedron: Asymmetry, vol. 3, No. 9, 1992; pp. 1157-1160.
Lynch, J.E., et al. “Synthesis of an HMG-CoA reductase inhibitor; a diastereoselective aldol approach” Tetrahedron Letters, vol. 28, No. 13, 1987, pp. 1385-1387.
Sletzinger, M., et al, “A diasterospecific, non-racemic synthesis of a novel beta-hydroxy-delta-lactone HMG-CoA reductase inhibitor” Tetrahederon Letters, vol. 26, No. 25, 1985, pp. 2951-2954.
Chen, K-M., et al; “1,3-Syn Diastereoselective Reduction of beta-hydroxyketones Utilizing Alkoxydialkylboranes” Tetrahedron Letters, vol. 28, No. 2, pp. 155-158.
Chen, K-M., et al; “A Novel Method for the In Situ Generation of Alkoxydialkylboranes and Their Use in the Selective Preparation of 1,3-Syn Diols,” Chemistry Letters, 1987 pp. 1923-1926.
Narasaka, N., et al; Stereoselective Reduction of Beta-hydroxyketones to 1,3-Diols, Tetrahedron, vol. 40, No. 12, 1984, pp. 2233-2238.
Brower, P., “The synthesis of (4R-cis)-1, 1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for the preparation of CI-981, a highly potent, tissue selective inhibitor of HMG-CoA reductase” Tetrahedron Letters, vol. 33, No. 17, 1992, pp. 2279-2282.
Paterson, I., “Towards the Synthesis of Swinholide A and Scytophycin C., A Highly Stereocontrolled Synthesis of (-)-Pre-Swinholide A” Tetrahedron Letters, vol. 35, No. 20, 1994, pp. 3405-3408.
Prasad, K., et al, “A Highly Steroselective Route to the Four Steroisomers of a Six-Carbon Synthon” Tetrahedron: Asymmetry, vol. 1, No. 5, 1990; pp. 307-310.
M. Sato et al., “Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines with Chiral Aldehydes: Enantioselective Synthesis of 1,3-Dioxin-4-ones Having a 2,3-Dihydroxlylated Alkyl Group at the 6-Position,” Tetrahedron Asymmetry, vol. 3, No. 9, 1992, pp. 1157-1160.
J.E. Lynch et al., “Synthesis of an HMG-CoA reductase inhibitor: a diastereoselective aldol approach,” Tetrahedron Letters, vol. 28, No. 13, 1987, pp. 1385-1388.
M. Sletzinger et al., “A diastereospecific non-racemic synthesis of a novel beta-hydroxy-delta-lactone HMG-CoA reductase inhibitor,” Tetrahedron Letters, vol. 26, No. 25, 1985, pp. 2951-2954.
K.-M. Chen et al., “1.3-SynDiastereoselective Reduction of beta-hydroxyketones Utilizing Alkoxydialkylboranes,” Tetrahedron Letters, vol. 28, No. 2, pp. 155-158.
K.-M. Chen et al., “A Novel Method for the In Situ Generation of Alkoxydialkylboranes and Their Use in the Selective Preparation of 1,3-SynDiols,” Chemistry Letters, 1987, pp. 1923-1926.
K. Narasaka et al., “Stereoselective Reduction of Beta-hydroxyketones to 1,3-Diols,” Tetrahedron, vol. 40, No. 12, 1984, pp. 2233-2238.
P. Brower, “The Synthesis of (4R-cis)-1,1-Dimethylethyl 6-cyanomethyl-2.2-dimethyl-1,3-dioxane-4-acetatc, a Key Intermediate for the Preparation of CI-981, a Highly Potent, Tissue Selective Inhibitor of HMG-CoA Reductase,” Tetrahedron Letters, vol. 33, No. 17, 1992, pp. 2279-2282.
I. Paterson, “Towards the Synthesis of Swinholide A and Scytophycin C. A Highly Stereocontrolled Synthesis of (-)-Pre-Swinholide A.,” Tetrahedron Letters, vol. 35. No. 20, 1994, pp. 3405-3408.
Prasad, K., et al, “A Highly Stereoselective Route to the Four Stereoisomers of a Six-Carbon Synthon”, Tetrahedron: Asymmetry, vol. 1, No. 5, 1990; pp. 307-310.

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