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Asymmetric synthesis and absolute stereochemistry of LY248686

✍ Scribed by Jack Deeter; Jeff Frazier; Gilbert Staten; Mike Staszak; Leland Weigel

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 331 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97251-4

No coin nor oath required. For personal study only.

✦ Synopsis

Reduction of 3-(dialkylamino)-1-aryl-t-propanones with a 2:l complex of [(2R,3S-(+)-4--dimethylamino-1,2-diphenyl-3-methyl-2-butanol] (8) and lithium aluminum hydride (LAH) provided the corresponding 1,Saminoalcohols in high ee's (SO-88%). This process was developed and applied to the synthesis of LY248686 (l), a potent inhibitor of serotonin (5HT) and norepinephrine (NE) uptake. Absolute configurations have been established by single crystal x-ray analysis. Recently, reports from Robertson and Wong have shown that a series of 3-(l-naphthoxy)-3arylpropanamines are potent inhibitors of the serotonin and norepinephrine uptake carriers'. Such

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