Potassium sodium tartarate → N-(4-(4-(Ethyl(2-cyclopentylethyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

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Reaction Steps

A 1M solution of LiAlH4 in THF (15.9 ml) was mixed with THF (15.9 ml) and cooled, under nitrogen in an ice bath. To this solution was added, dropwise, with stirring, a solution of the product from Step I (3.0 g, 0.0076 mol) in THF (30.7 ml). The mixture was kept in the ice bath for 1 hour and then treated cautiously with a saturated potassium sodium tartrate solution (16.1 ml). This mixture was stirred at ambient temperature for 45 minutes and extracted with EtOAc. The extract was washed with water, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 10-20% MeOH--CHCl3. A solution of the product in Et2O was washed with NaHCO3 and concentrated to give 1.86 g of the titled compound which is a compound of Formula I'. The mass spectrum had m/z 382 (M+). Theory for C20H34N2O3S: 382.2290; measured: 382.2291.

Provenance & Evidence