ASYMMETRIC SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF LY248686

Article abstract of DOI:10.1016/S0040-4039(00)97251-4

Reduction of 3-(dialkylamino)-1-aryl-1-propanones with a 2 : 1 complex of <(2R,3S-(+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol> (8) and lithium aluminum hydride (LAH) provided the corresponding 1,3-diaminoalcohols in high ee's (80-88percent).This process was developed and applied to the synthesis of LY248686 (1), a potent inhibitor of serotonin (5HT) and norepinephrine (NE) uptake.Absolute configurations have been established by single crystal x-ray analysis.