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Synthesis of rel-(3RS,3aSR,7aSR)-3-(4-Chlorophenyl)-3a,4,5,6,7,7a-hexahydro-1-methylindolin-6-one, the Main Metabolite of the Analgesic Ro 15-8081: A Potent Amine-Uptake Inhibitor

✍ Scribed by Michael Bös; Willy P. Burkard; Jean-Luc Moreau; Peter Schönholzer

Book ID: 102256378
Publisher: John Wiley and Sons
Year: 1990
Tongue: German
Weight: 411 KB
Volume: 73
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19900730421

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✦ Synopsis

Abstract

The synthesis of the title compound 2 and its diastereoisomer 3 was accomplished using tricarbonyl[1‐5‐n‐(4‐methoxycyclohexa‐2,4‐dien‐1‐yl)]iron tetrafluoroborate (4) as a precursor to the cyclohexanone ring. The assignments of the relative configurations of 2 and 3 are based on the X‐ray analysis of compound 3. Both compounds 2 and 3 are potent inhibitors of neuronal noradrenaline uptake in rats with similar potencies in vitro as compared to amitriptyline and desipramine. Compounds 2 and 3 are less potent as serotonin‐uptake inhibitors, very weak inhibitors of dopamine uptake, and virtually devoid of antinociceptive activity.

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