2-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid → 2-(2-Isobutyl-4-methyl-benzoylamino)-indan-2-carboxylic acid

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Reaction Steps

To a solution of 2-[4-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid (510 mg, 1.45 mmol) in glacial acetic acid (65 mL) under N2 is added Pd/C (10% Pd, 138 mg, 10 mol %). The reaction is hydrogenated at 60 psi H2 and 90° C. overnight. The reaction is cooled to RT and filtered through Celite, washing the filter cake with water (2×15 mL) and MeOH (2×15 mL); the filtrate is concentrated in vacuo. The residue is dissolved in water (75 mL) and extracted with EtOAc (2×30 mL). The combined organic layers are washed with a 5% NaHCO3 solution (3×20 mL), water (20 mL) and brine (20 mL) then dried over anhydrous Na2SO4. The organic layer is concentrated in vacuo to give product (280) as white solid (350 mg, 69%).

Provenance & Evidence