Potassium sodium tartarate → N-(4-(4-(Ethyl(4,4-dimethylpentyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

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Reaction Steps

A solution of the product from Step I (4.4 g, 0.0115 mol) in THF (46.4 ml) was added dropwise during 45 minutes, under nitrogen to a stirred, ice cold mixture of a 1M solution of LiAlH4 in THF (24.0 ml) and THF (24 ml). The mixture was kept in the ice bath for 45 minutes and then treated slowly with a saturated aqueous solution of potassium sodium tartrate (24.4 ml). This mixture was stirred for 30 minutes and extracted with EtOAc. The extracts were washed with water and brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 5-10% MeOH--CHCl3. The product was dissolved in Et2O, washed with NaHCO3, dried (MgSO4) and concentrated to give 2.96 of the titled compound. The FAB mass spectrum had m/z 385 (M+H)+. Theory for C20H37N2O3S: 385.2525; measured.: 385.2546.

Provenance & Evidence