Certain hexahydro-6-arylpyrrolo[2,1-A]isoquinolines
AssigneeMcNeilab, Inc.
InventorsBruce E. Maryanoff, Cynthia A. Maryanoff, David F. McComsey, Kirk L. Sorgi
Life of this patent
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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 trifuloroacetic acid.
Claims2
An enammonium salt of the following formula (X):
- ##STR11## wherein R.sub.4 and R.sub.5 are the same and both are hydrogen, or different and each is selected from the group of hydrogen or lower alkyl;
- R.sub.6 and R.sub.7 are the same or different and each is selected from the group hydrogen, lower alkyl, lower alkoxy, hydroxy, or halogen, or else are taken together as methylenedioxy;
- and
- R.sub.8 and R.sub.9 are selected from the group hydrogen, lower alkyl, perfluoro(lower)alkyl, lower alkoxy, carb(lower)alkoxy, lower alkylthio, lower alkylsulfonyl, nitro, or halogen;
- and
- X is an anion.
An iminium salt of the following formula (XI) ##STR12## wherein R.sub.4 and R.sub.5 are the same and both are hydrogen, or different and each is selected from the group of hydrogen or lower alkyl;
- R.sub.6 and R.sub.7 are the same or different and each is selected from the group hydrogen, lower alkyl, lower alkoxy, hydroxy, or halogen, or else are taken together as methylenedioxy;
- and
- R.sub.8 and R.sub.9 are selected from the group hydrogen, lower alkyl, perfluoro(lower)alkyl, lower alkoxy, carb(lower)alkoxy, lower alkylthio, lower alkylsulfonyl, nitro, or halogen;
- and
- X is an anion.
Dependencies are inferred from the claim text.