Process for the stereospecific synthesis of indole derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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548231, 548507, 548467, C07B 5300, C07D20916, C07D40312, C07D40512

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048066559

ABSTRACT:
The present invention relates to a process for the stereo-specific synthesis of indole derivatives of formula: ##STR1## which consists in using 3-tosyloxy-1,2-O-isopropylidenepropane-1,2-diol (II) in an optically pure form in order to introduce the asymetric carbon C* of compound (I). Compound (II) is condensed with a suitable primary amine in order to prepare an oxazolidinone and condensation with a suitable phenol, and the oxazolidinone ring is then opened to form an indole compound (I).

REFERENCES:
patent: 4234595 (1980-01-01), Kreighbaum
patent: 4404217 (1987-09-01), Demarne
patent: 4510315 (1985-04-01), Demarne
patent: 4522824 (1985-06-01), Wagnon
Schwender, J. Med Chem 13, 634 (1970).

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