Ethyl orthoformate → HCID 67517614, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-amino-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate (365 mg, 1.90 mmol), triethyl orthoformate (451 mg, 3.04 mmol), and sodium azide (185 mg, 2.85 mmol) in acetic acid (8 mL) was maintained in an oil bath heated at 80° C. for 3 h. After cooling to room temperature, the mixture was diluted with water and ethyl acetate and the layers separated. The aqueous was extracted with ethyl acetate (2×) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the resulting residue (8−>80% EtOAc/hexanes eluent) provided methyl 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate. 1H NMR (500 MHz, CDCl3), δ 9.54 (s, 1H), 8.55 (s, 1H), 8.00 (s, 1H), 4.22 (m, 1H), 3.82 (s, 3H), 3.30-3.06 (m, 2H), 2.66-2.49 (m, 2H); LC/MS (M+1)+=193.0;

Provenance & Evidence