Benzyl chloroformate → Dibenzyl azetidine-1,2-dicarboxylate

Participants

Reaction Steps

Benzyl azetidine-2-carboxylate (4.0 g, 21 mmol) and potassium carbonate (5 g, 36 mmol) in a mixture of 1,4-dioxane (25 ml) and water (30 ml) was treated with benzyl chloroformate (3 ml, 21 mmol) at room temperature for 6 hours. Piperazine (5 drops) was added and the mixture was stirred for additional 0.5 hour. The organic volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and 2 N HCl solution. The upper layer was washed with brine and dried over MgSO4. Removal of solvents afforded the desired compound (6.8 g, Yield: 96%). MS (DCI/NH3) m/z 278 (M+H)+.

Provenance & Evidence