Sodium Chloride → (R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester

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Reaction Steps

To (R)-5-formyl-2,2-diphenylmorpholine-4-carboxylic acid tert-butyl ester (1.03 g, 2.80 mmol) and 1,3-difluoro-5-(2-nitroethyl)-benzene (0.577 g, 3.08 mmol) in tetrahydrofuran (5 mL) at −0° C. under nitrogen add tetrabutylammonium fluoride (3 mL, 3.0 mmol, 1.0 M in tetrahydrofuran). Stir 20 minutes and add half saturated aqueous sodium chloride (20 mL) and ethyl acetate (100 mL). Separate the layers and wash the organic layer with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 50:50 ethyl acetate:hexanes, then re-crystallize from hexanes/dichloromethane to give the desired compound.

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