1-Nitro-2-phenylethane → (2R,4S)-tert-butyl 4-fluoro-2-((1R,2S)-1-hydroxy-2-nitro-3-phenylpropyl)pyrrolidine-1-carboxylate

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Reaction Steps

Add tetrabutylammonium fluoride (2.0 mL of 1.0 M solution in THF) to an ice-cold solution of 1-phenyl-2-nitroethane (0.51 mL, 3.79 mmol) in THF (2 mL). Stir 5 min and add 4-(S)-fluoro-2-(R)-formylpyrrolidine-1-carboxylic acid tert-butyl ester (0.58 g, 1.95 mmol) in THF (6 mL). Stir 90 min, dilute with ethyl acetate, wash with water (3×50 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compounds as foams, 4-(S)-fluoro-2-(R)-(1-(S)-hydroxy-2-(S)-nitro-3-phenylpropyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.21 g, 29%) and 4-(S)-fluoro-2-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.33 g, 46%).

Provenance & Evidence