Imidazole → Tert-butyl 3-iodoazetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (3.35 g, 19.3 mmol) in toluene (200 mL) was added imidazole (3.95 g, 58.0 mmol), triphenylphosphine (10.1 g, 38.7 mmol) and iodine (7.36 g, 29.0 mmol). The mixture was heated for 100° C. for 1 h, cooled to room temperature, then poured into sodium bicarbonate aqueous solution (30 mL). Excess triphenylphosphine was destroyed by addition of iodine until iodine coloration persisted in organic layer. The organic layer was separated and washed with saturated sodium thiosulfate aqueous solution, dried over sodium sulfate. The crude product was purified by silica gel column chromatography (hexane-ethyl acetate=9:1 to 1:1) to gave the title compound (5.42 g, 99%) as clear oil.

Provenance & Evidence