Ethyl orthoformate → HCID 67517270, compound

Participants

Reaction Steps

A solution of 5-aminoindane-1-carboxylic acid (2.95 g, 16.7 mmol), sodium azide (1.20 g, 18.3 mmol) and triethyl orthoformate (7.42 g, 50.1 mmol) in 20 mL of acetic acid was heated to 100° C. for 3 hrs. After the reaction was completed, the mixture was cooled to ambient temperature. The solution was removed under vacuum and the residue was diluted with EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified via silica gel column chromatography to give the crude product, which was re-crystallized from DCM to yield 5-(1H-tetrazol-1-yl)indane-1-carboxylic acid. 1H-NMR (400 MHz, DMSO) δ ppm 10.0 (s, 1H), 7.75 (s, 1H), 7.66-7.69 (m, 1H), 7.55 (d, J=8.1 Hz, 1H), 4.02-4.06 (m, 1H), 2.88-3.08 (m, 2H), 2.31 (q, J=8.1 Hz, 2H).

Provenance & Evidence