Method of preparing optically pure precursors of paroxetine

Details Method of preparing optically pure precursors of paroxetine Method of preparing optically pure precursors of paroxetine

1992-08-06

1993-11-02

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21122

Patent

active

052585174

ABSTRACT:
A biocatalytic method of preparing optically pure precursors of paroxetine and a method of preparing paroxetine therefrom are disclosed. A racemic trans ester precursor compound of paroxetine is first prepared. The racemic trans ester precursor compound comprises a mixture of (3S,4R) and (3R,4S) enantiomers. The (3R,4S) enantiomer is hydrolyzed biocatalytically to the corresponding (3R,4S)-trans carboxylic acid or alternatively, the (3S,4R) enantiomer is biocatalytically hydrolyzed the to (3S,4R)-trans carboxylic acid in a reaction catalyzed by a isolated enzyme or a microorganism. In the first instance, the unhydrolyzed (3S,4R) enantiomer is separated from the (3R,4S)-trans carboxylic acid, whereas in the second instance the (3S,4R)-trans carboxylic acid is separated from the unhydrolyzed (3R,4S) enantiomer. The (3S,4R) enantiomer obtained following the selective hydrolysis is reduced to form a (-)-trans-(3S,4R) primary alcohol precursor of paroxetine. Paroxetine is then formed from the (-)-trans-(3S,4R) primary alcohol precursor.

REFERENCES:
patent: 3912743 (1975-10-01), Christensen et al.
patent: 4007196 (1977-02-01), Christensen et al.
patent: 4902801 (1990-02-01), Faruk et al.

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