Benzyl Bromide → (R)-4-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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Reaction Steps

Add sodium hydride (4.4 g, 110 mmol, 60% in mineral oil) portionwise to a room temperature maintained solution of (R)-4-[(1S,2S)-2-dibenzylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (50.5 g, 89.222 mmol) and benzyl bromide (22 mL, 184.96 mmol) in N,N-dimethylformamide (400 mL). Stir for 15 minutes and pour into saturated aqueous ammonium chloride. Extract with ethyl acetate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 2:98 to 4:96 ethyl acetate:hexanes) to give the title compound as a viscous oil that solidifies upon standing (48.5 g, 83%).

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