Method for preparing optically active 5-hydroxy-3-(4'-hydroxyphe

Details Method for preparing optically active 5-hydroxy-3-(4'-hydroxyphe Method for preparing optically active 5-hydroxy-3-(4'-hydroxyphe

1997-10-24

1999-09-28

Kumar, Shailendra

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

Organic compounds

Oxygen containing

568721, 568727, 568732, 568734, 435197, C07C 3711, C07C 3720, C07C 3912, C12N 918

Patent

active

059591595

ABSTRACT:
A process for resolving racemic diesters of (R,S)(.+-.)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane is disclosed. The process utilizes a microbial enzyme derived from Chromobacterium viscosum to catalyze the enantioselective and regioselective hydrolysis of the (S)(-)-enantiomer of the racemic mixture to its corresponding monoester at a faster rate than the (R)(+)-enantiomer. A substantially pure (S)(-)-indane monoester is thereby formed, while the (R)(+)-indane diester remains unreacted. The (S)(-)-monoester and the (R)(+)-diester can then be hydrolyzed using conventional techniques to form optically active (R)(+)- and (S)(-)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane enantiomers for use as monomers in the synthesis of chiral polymers.

REFERENCES:
patent: 2979534 (1961-04-01), Petsopoulas et al.
patent: 4334106 (1982-06-01), Dai
patent: 4879421 (1989-11-01), Kazlauskas
patent: 5703197 (1997-12-01), Gordon et al.
patent: 5777063 (1998-07-01), Gordon et al.
Lang et al., "Crystal Structure of a Bacterial Lipase from Chromobacterium viscosum ATCC 6918 Refined at 1.6 A Resolution", J. Mol. Biol. 259, 704-717 (1996).
K. Laumen and M. Schneider, "A Facile Chemoenzymatic Route to Optically Pure Building Blocks for Cyclopentanoid Natural Products", J. Chem. Soc., Chem. Commun. 1298-1299 (1986).

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