Ethyl orthoformate → HCID 67517946, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-amino-5,6,7,8-tetrahydroquinoline-5-carboxylate (850 mg, 4.12 mmol) was stirred in acetic acid (15 ml) and tri-ethyl orthoformate (1.373 ml, 8.24 mmol) followed by sodium azide (482 mg, 7.42 mmol) then heated to 80° C. for 3 hrs. The reaction was cooled and evaporated to dryness. The mixture was taken up in DCM and washed with saturated NaHCO3 solution, then with brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed through a 40 g ISCO Redi-sep column and eluted with ethyl acetate:hexane (2:3) to yield methyl 2-(1H-tetrazol-1-yl)-5,6,7,8-tetrahydroquinoline-5-carboxylate. 1H-NMR (600 MHz, DMSO): δ ppm 10.07 (s, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 4.06 (t, J=5.4 Hz, 1H), 3.65 (s, 3H), 2.83-2.93 (m, 2H), 2.07-2.12 (b, 1H), 1.95-2.0 (m, 1H), 1.86-1.90 (m, 2H).

Provenance & Evidence