Process for the preparation of (-)-3,4-trans-diarylchromans

Details Process for the preparation of (-)-3,4-trans-diarylchromans Process for the preparation of (-)-3,4-trans-diarylchromans

1997-10-27

1999-07-20

Powers, Fiona T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549406, C07D31158, C07D40512

Patent

active

059257717

ABSTRACT:
Disclosed is a process for preparing (-)-3,4-trans-diarylchromans of formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification. This process involves reacting a (+,-)-3,4-cis-diarylchroman with a chiral acid in an inert organic solvent to obtain the chiral acid salt of the (-)-3,4-cis enantiomer in crystalline form, subjecting the crystalline salt to hydrolysis, and rearranging the (-)-3,4-cis enantiomer to the (-)-3,4-trans enantiomer with a strong base in an inert aprotic solvent.

REFERENCES:
patent: 3340276 (1967-09-01), Carney et al.
patent: 4447622 (1984-05-01), Salman et al.
Saeed et al., Chemical Abstracts, 102:40068, 1985.
Salman et al., J. Med. Chem., 26, pp. 592-595, (1983).
Ray et al., J. Med. Chem., vol. 19, No. 2, pp. 276-279, (1976).

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