Azidobenzene → 1-Tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

Participants

Reaction Steps

A mixture of the crude phenylazide (1.37 g, 11.5 mmol) from above and 1-tert-butoxycarbonyl-4-ethynyl-1,2,3,6-tetrahydropyridine (2 g, 9.6 mmol) (Example 1) in toluene (20 ml) was refluxed for 24 hours. The reaction was cooled and the solvent evaporated in vacuo. The crude residue was chromatographed on silica eluting with ethyl acetate/petrol (60°-80° C.) (1:2) to give the 1-tert-butoxycarbonyl-4-(1-phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine as a tan waxy solid (853 mg, 27%), δH (CDCl3) 1.49 (9H, s, OC(CH3)3), 2.59 (2H, br s, tetrahydropyridinyl CH2), 3.67 (2H, t, J 5.2 Hz, tetrahydropyridinyl CH2), 4.12 (2H, br s, tetrahydropyridinyl CH2), 6.53 (1H, br s, tetrahydropyridinyl 5-H), 7.42-7.46 (1H, m, ArH), 7.51-7.55 (2H, m, ArH), 7.72-7.75 (2H, m, ArH), 7.87 (1H, s, triazolyl 5-H).

Provenance & Evidence