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

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (25-3) (3.5 g, 0.02 mol) in toluene (200 mL) was treated with imidazole (4.08 g, 0.06 mol), PPh3 (0.6 g, 0.04 mol), and I2 (7.62 g, 0.03 mol). The mixture was heated at 100° C. for 1 h and cooled down to room temperature. It was then poured into saturated NaHCO3 solution (30 mL). Excess PPh3 was destroyed by addition of iodine until I2 coloration persisted in organic layer. The mixture was washed with 5% Na2SO3 solution, dried over Na2SO4, and evaporated in vacuo. The residue was purified on silica gel column to give 199a (5.31 g, 93%). MS: [M+H]+ 284.

Provenance & Evidence