Acetone → Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of 1-(t-butoxycarbonyl)piperidin-4-yl methanesulfonate (13.58 g, 46.4 mmol) and sodium iodide (34.68 g, 232 mmol) in acetone (80 mL) was heated to reflux for 3 h. The mixture was partitioned between ether (350 mL) and H2O (350 mL). The organic layer was washed with saturated aq. NaCl (250 mL), and the aqueous layers were extracted in succession with ether (250 mL). The combined organic layers were dried (Na2SO4), decanted, and evaporated to give 14.8 g of 1-(t-butoxycarbonyl)-4-(iodomethyl)piperidine as a pale yellow oil. 1H NMR (500 MHz) δ 4.25-4.00 (m, 2H), 3.12 (d, J=4, 2H), 2.78-2.52 (m, 2H), 1.85 (d, J=13, 2H), 1.68-1.56 (m, 1H), 1.48 (s, 9H), 1.15 (qd, J=12, 4, 2H).

Provenance & Evidence