METHOD OF PRODUCING COREY LACTONE ENANTIOMERIC DERIVATIVES Russian patent published in 2013 - IPC C07D307/935 

Abstract RU 2501793 C2

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, specifically to a method of producing Corey lactone enantiomeric derivatives of formulae (-)-Ia,b and (+)-Ia,b, which involves reacting racemic 5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one with trialkyl-chlorosilane, followed by acetalisation of the obtained derivatives with (-)-(1R,4R,5S)-4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one while boiling in anhydrous benzene in the presence of a para-toluene sulphonic acid catalyst to form diastereomeric esters which are separated by column chromatography on silica gel, wherein methanolysis of said esters is carried out by boiling in methanol in the presence of a catalyst of a pyridinium salt para-toluene sulphonic acid for 1-1.25 hours. The disclosed method enables to obtain enantiomerically pure desired compounds ((-)-Ia-c) and ((+)-Ia-c) with total output of 20-25% with respect to the starting (±)-lactone diol (II) and enantiomeric purity of ≥97%.

EFFECT: improved method.

5 cl, 12 ex

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RU 2 501 793 C2

Authors

Loza Vladimir Valer'Evich

Vostrikov Nikolaj Sergeevich

Miftakhov Mansur Sagar'Jarovich

Dates

2013-12-20Published

2011-05-20Filed