Imidazole → Benzyl 4-(2-iodoethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 3-2(263 g, 116 mmol) was treated with triphenylphosphine (33.5 g, 128 mmol), imidazole (11.9 g, 175 mmol) and cooled to 0° C. Iodine (32.4 g, 128 mmol) was added and the ice bath was removed. The reaction was filtered into a separatory funnel and the solution was washed with H2O and brine, dried over MgSO4 and concentrated. The residue was chromatographed (10% EtOAc/Hexanes) to give 3-3 as a colorless oil. Rf (20% EtOAc/Hexanes) 0.56 1H NMR (300 MHz, CDCl3) δ 7.4-7.1 (m, 5H), 5.2-5.05 (bs, 2H), 4.3-4.1 (bs, 2H), 3.2 (t, 2H), 2.8 (bs, 2H), 1.8-1.5 (m, 5H), 1.15 (m, 2H). ##STR31## 2(N-t-Butyloxycarbonylaminopiperidin-4-yl)ethanol (4-1)

Provenance & Evidence