1,2-Dichloroethane → benzyl 3-(1-methyl-1H-benzimidazol-2-yl)azetidine-1-carboxylate

Participants

Reaction Steps

1-2 (3.0 g, 12.75 mmol) was dissolved in THF (64 mL) and N-methylbenzene-1,2-diamine (2.02 g, 16.58 mmol), EDC (2.93 g, 15.30 mmol), HOAt (2.08 g, 15.30 mmol), and Hunig's base (6.7 mL, 38.3 mmol) were added. After stirring for 18 hours at ambient temperature, the reaction solution was concentrated. The residue was then dissolved in acetic acid (30 mL). After stirring at ambient temperature for 2 hours, the solvent was removed. The residue was partitioned between ethyl acetate and 5% aqueous NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (EtOAc/Hexanes) to provide 1-3 as a off-white solid (3.32 g, 81%). MS: m/z=322.4 (M+H).

Provenance & Evidence