Imidazole → 4-(N-BOC-Piperidin-4-yl)butyl iodide

Participants

Reaction Steps

A mixture of 4-2 (3.4 g, 13.2 mmol), Ph3P (5.2 g, 19.8 mmol), imidazole (2.7 g, 39.6 mmol), and THF (30 mL) at ambient temperature was treated with iodine (5.0 g, 19.8 mmol) in three portions. After 1 h most of the THF was evaporated and the residue partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, 10% Na2S2O3, and brine, dried (MgSO4) and concentrated to give a solid. Flash chromatography (silica, 10% EtOAc/hexanes) gave 4-3 (3.0 g) as a light yellow oil. Rf 0.27 (silica, 10% EtOAc/hexanes).

Provenance & Evidence