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

Participants

Reaction Conditions

Reaction Steps

A solution of 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (3.35 g, 19.34 mmol) in toluene (200 ml) was treated with imidazole (3.95 g, 58.01 mmol), triphenyl-phosphine (10.14 g, 38.65 mmol) and I2 (7.36 g, 28.99 mmol). The mixture was heated at 100° C. for 1 h, cooled down to room temperature and subsequently poured into a saturated aqueous solution of NaHCO3 (30 ml). Excess triphenylphosphine was destroyed by addition of iodine until I2 coloration persisted in organic layer. The latter was washed with an aqueous solution of Na2S2O3 (5% strength), dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (heptane:EtOAc, 2:1) provides the title compound (5.19 g, 95%) as a light yellow oil.

Provenance & Evidence