Hydrogen Peroxide → (2S)-4-methyl-2-({(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)-1,1'-biphenyl-4-yl]ethyl}amino)pentan-1-ol

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Reaction Steps

To a 0° C. solution of the sulfide (19 g) from Step 4 in toluene (400 mL) was added Na2WO4.2H2O (0.16 g) and Bu4NHSO4 (0.81 g). Then 30% hydrogen peroxide (12.2 mL) was slowly added and the mixture was stirred at room temperature for 4.5 hours. The mixture was poured slowly on a mixture of ice, dilute aqueous sodium thiosulfate and ethyl acetate. The organic layer was separated and the aqueous further extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine, dried with magnesium sulfate and the solvent were removed in vacuo to yield a residue which was purified on SiO2 using ethyl acetate and hexanes (1:1) as eluant to yield the product.

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