Imidazole → HCID 21180602, compound

Participants

Reaction Steps

A solution of 4-(2-hydroxyethyl)-1-(t-butoxycarbonyl)-piperidine (4.5 g, 19.6 mmol, from EXAMPLE 113, Step A), imidazole (1.8 g, 27 mmol) and triphenylphosphine (7.1 g, 27 mmol) in 60 mL of 2:1 v/v ether/CH3CN at 0° C. was treated with 7.4 g (29 mmol) of iodine. The mixture was warmed to rt and stirred for 15 min. The mixture was diluted with 200 mL of ether and washed with sat'd Na2SO4 (2×200 mL), sat'd CaSO4 (100 mL) and sat'd NaCl. The organic phase was dried over Na2SO4 and concentrated. The material was filtered through a pad of silica to remove the triphenylphosphine oxide providing 6.1 g (92%) of the title compound: 1H NMR (300 MHz) δ 1.0-1.2 (m, 2H), 1.45 (s, 9H), 1.55 (m, 1H), 1.7-1.8 (m, 4H), 2.6-2.8 (m, 2H), 3.19-3.25 (t, 2H), 4.04.2 (m, 2H).

Provenance & Evidence