4-Isopropylaniline → 4-tert-Butoxycarbonylamino-4-(4-isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

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Reaction Steps

A mixture of 3.78 g (10 mmol) 4-tert-Butoxycarbonylamino-piperidine-1,4-dicarboxylic acid monobenzyl ester (commercially available), 1.76 g (13 mmol) 4-isopropyl-aniline (commercially available), 2.1 g (11 mmol) EDCI and 1.36 g (11 mmol) DMAP in 50 mL THF was stirred at room temperature over night. After concentration of the mixture ethyl acetate and water was added. The mixture was extracted with ethyl acetate and the combined organic fractions were dried with MgSO4 and evaporated. The residue was purified over silica eluting with a gradient formed from ethyl acetate and hexane to afford after evaporation of the product containing fractions 2.85 g (57%) of the title compound as white solid. MS (m/e): 496.3 [(M+H)+].

Provenance & Evidence