Phthalimide → N-[[1-[2-(Methoxycarbonyl)phenyl]piperidin-3-yl]methyl]phthalimide

Participants

Reaction Steps

Triphenylphosphine (1.68 g, 6.20 mmol) and phthalimide (799 mg, 5.43 mmol) were added to methyl 2-[3-(hydroxymethyl)piperidin-1-yl]benzoate (1.29 g, 5.17 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 10 min and a 40% diethyl azodicarboxylate/toluene solution (3.52 mL, 7.76 mmol) was added. The mixture was then stirred at room temperature for 8 hours. Subsequently, water was added and the mixture was extracted with ethylacetate. The extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 1.85 g (95%) of the desired compound as a pale yellow oil.

Provenance & Evidence