Potassium sodium tartarate → N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

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Reaction Steps

The product from Step I (3.0 g, 0.010 mol) was added in small portions, under nitrogen to a stirred, ice-cold mixture of LiAlH4 (1.15 g, 0.030 mol) in THF (75 ml). This mixture was kept in the ice bath for 1 hour and at ambient temperature for 2 hours. It was then mixed with an additional 100 ml of THF, refluxed for a few minutes and kept at ambient temperature for 18 hours. The mixture was treated carefully with 69 ml of a saturated sodium potassium tartrate solution and stirred for 1 hour. It was extracted with EtOAc. The extract was washed with a dilute sodium chloride solution. The aqueous layer contained the product; it was concentrated and finally freeze-dried. The resulting solid was extracted with MeOH. The methanol solution was concentrated and the residue extracted with CH2Cl2. The CH2Cl2 solution was concentrated to give 1.6 g of crude product that was purified by chromatography on silica gel with 1% NH4OH-10 to 20% MeOH--CHCl3. The product was crystallized from MeOH--EtOAc to give 540 mg of N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide, mp 174°-176° C. The analytical sample was crystallized from MeOH and had mp 178.5°-180.5° C. Anal. calc'd for C13H22N2O3S: C, 54.52; H, 7.74; N, 9.78; S, 11.20. Found: C, 54.40; H, 7.84; N, 10.00; S, 11.02.

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