Process for the manufacture of organic compounds

Details Process for the manufacture of organic compounds Process for the manufacture of organic compounds

2004-07-14

2009-08-11

Padmanabhan, Sreeni (Department: 1617)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S174000

Reexamination Certificate

active

07572917

ABSTRACT:
A method for preparing an alkali metal salt comprising: (a) condensing a disilyloxydiene with an aldehyde in the presence of a titanium (IV) catalyst in an inert solvent to form a 5(S)-hydroxy-3-ketoester; (b) reducing the 5(S)-hydroxy-3-ketoester to a 3(R),5(S)-dihydroxyester in the presence of a di(lower alkyl)methoxyborane; and (c) hydrolyzing the 3(R),5(S)-dihydroxyester in the presence of an aqueous base to form an alkali metal salt.

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Suzuki et al., “First Systematic Chiral Syntheses of Two Pairs of Enantiomers with 3,5-Dihydroxyheptenoic Acid Chain, Associated with a Potent Synthetic Statin NK-104”, Bioorganic & Medicinal Chemistry Letters, vol. 9, pp. 2977-2982 (1999).
Soriente, A, “An efficient asymetric aldol reaction of Chan's diene promoted by chiral ti(IV)-binol complex”, Tetrahedron: Asymetry., vol. 12, pp. 959-963, XP004241721, Apr. 2001.
Soriente et al., “Enantioselective aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene promoted by chiral Ti(IV)/BINOL complex”, Tetrahedron: Asymmetry, vol. 11, Issue 11, pp. 2255-2258, (2000).

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