Ugi reaction

1-cyclohexenyl isocyanide (47 mg, 50.2 µL,0.44 mmol) was added to a solution of propionic acid (33 mg, 32.9 µL,0.44 mmol), aniline (41 mg, 40.1 µL, 0.44 mmol), 4-phenylethylpiperidone (90 mg, 0.44 mmol) in MeOH (2.2 mL) at room temperature and the solutionwas heated at 55 C and stirred for 24 h. The solvent was removed underreduced pressure, and the residue was dissolved in EtOAc (5 mL). The organic solution was washed with sat aq NaHCO3 (2 2.5 mL) and brine (2.5 mL) and dried (MgSO4), and the solvent was removed under reduced pressure. The crude product was purified either via HPLC/MS preparative with gradient starting from 10% MeOH / 90% H2O / 0.1% ammonia reaching 100% MeOH / 0.1%ammonia. The product was obtained in 82% yield (165 mg).

 

Reference: Tetrahedron Letters Volume 51, Issue 22, 2 June 2010, Pages 2983-2985

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