1H-Benzimidazole, 1-methyl- → Tert-butyl 3-(1-methylbenzimidazol-2-yl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added to a stirred solution of 1-methylbenzimidazole 1g (100 mg, 1.0 mmol), concentrated H2SO4 (108 μL, 1.0 mmol), 1-Boc-3-(iodo)azetidine (566 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (5 mL) at room temperature. The mixture was stirred at room temperature for 120 min, then diluted with EtOAc and saturated NaHCO3. The aqueous and organic layers were partitioned and the organic layer was washed with brine, dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / hexanes (3:7 to 7:3) as eluent to give the desired product 3f(52 mg, 17%) as a solid.

Provenance & Evidence