Acetic Acid → tert-butyl 5-(1H-tetrazol-1-yl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-aminohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (1.0 g, 4.4 mmol) and triethylorothoformate (4.4 mL, 26.4 mmol) in acetic acid (20 mL) was added sodium azide (1.7 g, 26.4 mmol) and the resulting mixture was set under inert atmosphere. The mixture was heated at 100° C. for 4 h and then cooled to RT at which time the volatiles were removed in vacuo. The residue was taken up in ethyl acetate (100 mL) and washed with aqueous sodium bicarbonate solution, followed by brine. The organics were dried over sodium sulfate, filtered, and concentrate to dryness under vacuum. The residue was placed in the refrigerator overnight and the next day a solid white precipitate was observed. The precipitate was triturated with hexane and the solvent was carefully decanted to give the pure product (675 mg, 55%) as a white solid. EST-MS calculated for C13H21N5O2: Exact Mass: 279.28. Found 280.28 (MH) and 302.27 (MNa)+.

Provenance & Evidence