Potassium Iodide → Tert-butyl 3-iodoazetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-[(methylsulphonyl)oxy]-1-azetidinecarboxylate (Synlett; 1998; 379), (5.0 g, 19.9 mmol), and potassium iodide (16.5 g, 99.4 mmol) in N,N-dimethylformamide (25 ml), was heated at 100° C. for 42 hours. The cooled mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was dried (MgSO4), concentrated under reduced pressure and the residue azeotroped with xylene. The crude product was purified by column chromatography on silica gel using dichloromethane as eluant, to give the title compound, 3.26 g.

Provenance & Evidence