Hydrochloric Acid → 4-[[(1R)-3-(4-Morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide

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Reaction Steps

(R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide (INTERMEDIATE 68, 2.01 g, 3.5 mmol) was dissolved in a solution of borane-THF complex (1M in THF, 8.0 ml, 8.0 mmol) and the resulting solution was stirred at room temperature overnight. The flask was opened to atmosphere and cautiously treated with MeOH (4.0 ml) followed by concentrated HCl (1.55 ml). The resulting mixture was heated at reflux for 3 hours and was then allowed to cool to room temperature. The pH of the mixture was adjusted to approximately 10 by the addition of aqueous solution of Na2CO3 (2 M) resulting in a precipitate. The mixture was dissolved in EtOAc (250 ml) and washed with water (125 ml), brine (125 ml), and dried (Na2SO4). Evaporation of the volatiles under reduced pressure afforded a concentrate, which was purified by column chromatography (ISCO, 80 g silica gel column, eluting with 0→100% EtOAc/hexanes) to provide the title product (1.33 g, yield: 68%).

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