Stereoselective reaction for hexahydro-6-arylpyrrolo(2,1-A) isoq

Details Stereoselective reaction for hexahydro-6-arylpyrrolo(2,1-A) isoq Stereoselective reaction for hexahydro-6-arylpyrrolo(2,1-A) isoq

1988-02-16

1989-06-06

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 65, C07D45500

Patent

active

048373281

ABSTRACT:
A diastereoselective process for known antidepressive compounds (I) via reduction of the corresponding alcohol (VII): ##STR1## whereby the product mixture of diastereomers is surprisingly and unexpectedly rich in the content of the trans configuration (II) over the cis configuration (III) as defined in the following formulae: ##STR2## The preferred reaction conditions include use of a borane complex as the reducing agent and an acidic solvent such as trifluoroacetic acid.

REFERENCES:
patent: 4595688 (1986-06-01), Maryanoff
Maryanoff, B. E. et al., J. Med. Chem. 1987, 30, 1433.
Maryanoff, B. E. et al., J. Org. Chem., 1987, 45, 355.
Maryanoff, B. E. et al., Drugs of the Future, 1986, 11, 18.
Maryanoff and McComsey, J. Heterocyclic Chem., 1985, 22, 911.
H. Brunner et al., Agnew. Chem. Int. Ed. Engl. 1985, 24, 995.

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