Sulfuric Acid → HCID 66874574, compound

Participants

Reaction Steps

Borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 3.09 mL, 3.09 mmol) was added at 0° C. to a solution of 8-(methyl-phenyl-carbamoyl)-octanoic acid methyl ester (300 mg, 1.03 mmol) in tetrahydrofuran (20 mL) The reaction mixture was stirred at room temperature overnight. A further aliquot of borane-tetrahydrofuran complex (2.1 mL, 2.1 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. Methanol (60 mL) was added followed by concentrated sulfuric acid. The reaction mixture was refluxed at 80° C. for 2 hours. After cooling to room temperature, saturated sodium carbonate was added and the reaction mixture was extracted 3 times with dichloromethane. The combined organic layers were dried over sodium sulfphate, filtered and the solvent was removed in vacuo. The crude product was purified by chromatography (SiO2; heptane-ethyl acetate gradient) to afford 9-(methyl-phenyl-amino)-nonanoic acid methyl ester (89 mg, 31%).

Provenance & Evidence