Imidazole → tert-Butyl (4-iodobutyl)carbamate

Participants

Reaction Steps

To a suspension of PPh3-resin (16.4 g, 21.1 mmol) in methylene chloride (150 mL) at 0° C. is added iodine (5.4 g, 21.2 mmol) and imidazole (1.66 g, 24.4 mmol) then stirring is continued at 0° C. for 45 min. To this is added (4-hydroxybutyl)-carbamic acid tert-butyl ester (2.0 g, 10.6 mmol) and the suspension is refluxed for 2 h. The suspension is filtered and the organic layer is washed with a saturated sodium bisulfite solution, water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as pale yellow liquid: 1H NMR (CDCl3) δ 4.51 (s, 1H), 3.21-3.17 (t, J=6.82 Hz, 2H), 3.16-3.11 (q, J=6.82 Hz, 2H), 1.88-1.81 (m, 2H), 1.62-1.55 (m, 2H), 1.43 (s, 9H).

Provenance & Evidence