Lithium aluminum hydride → Propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amide

Participants

Reaction Steps

To 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester (65, 3.80 g, 13.8 mmol) in tetrahydrofuran (133 mL) was added lithium tetrahydroaluminate (1.00 M in tetrahydrofuran, 20.0 mL, 20.0 mmol) under an atmosphere of nitrogen at room temperature. The reaction was stirred at room temperature for 8 hours, followed by addition of 10 g of NaSO4.10H2O. After 12 hours, the reaction was filtered, concentrated and purified with silica gel column chromatography eluting with 5% methanol in methylene chloride to give a white solid (66, 3.0 g, 87.9%).

Provenance & Evidence