Ammonium Chloride → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-4-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

Add (trifluoromethyl)trimethylsilane (0.28 mL, 1.88 mmol) to an ice cold solution of (R)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (0.50 g, 1.11 mmol) in tetrahydrofuran (10 mL). Add tetrabutylammonium fluoride (0.035 mL of 1M solution in tetrahydrofuran). Stir 2.5 hours and add tetrabutylammonium fluoride (2 mL of 1M solution in tetrahydrofuran) and stir 2 hours. Add saturated aqueous ammonium chloride (3 mL) and dilute with ethyl acetate and water. Wash organic layer with saturated aqueous sodium chloride, dry with magnesium sulfate and purify on silica gel with dichloromethane/ethyl acetate mixtures to give the desired compound and 10% hydroxy diastereomer as a foam (0.48 g, 83%).

Provenance & Evidence