Tetrabutylammonium Fluoride → (2R,5R)-5-[(1R,2S)-3-(3-Chloro-5-fluorophenyl)-1-hydroxy-2-nitropropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Add 1-chloro-3-fluoro-5-(2-nitroethyl)-benzene (0.343 g, 1.68 mmol) in dry tetrahydrofuran (2 mL) to a solution of (2R,5R)-2-(2,2-dimethylpropoxy)-5-formylmorpholine-4-carboxylic acid tert-butyl ester (0.462 g, 1.53 mmol) in tetrahydrofuran (7 mL). Add tetrabutylammonium fluoride (0.77 mL, 0.765 mmol, 1.0 M in tetrahydrofuran) and stir at room temperature for 1 hour. Dilute with ethyl acetate and wash with saturated aqueous sodium chloride, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 2:98 ethyl acetate:dichloromethane) to give the desired compound as a white foam (0.455 g, 59%).

Provenance & Evidence