Ethyl orthoformate → methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a flask charged with methyl 2-amino-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate (500 mg, 2.6 mmol) and a stir bar was added sodium azide (340 mg, 5.2 mmol), triethyl orthoformate (2.2 mL, 13 mmol), and HOAc (10 mL). The mixture was heated to 100° C. for 2 hours. The solvent was removed on a rotavapor, and the residue was taken into aq. Sodium carbonate, extracted with EtOAc (50 Mk×3), dried over sodium sulfate, and purified by MPLC (DCM-MeOH). After removal of solvent, an off-white solid was collected as the desired methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate. LC-MS (IE, m/z): 248 [M+1]+;

Provenance & Evidence