1-Butyne → N-Benzyl-3-(4,5-dimethyl-1,2,3-triazol-1-yl)pyrrolidine

Participants

Reaction Steps

To a solution of N-benzyl-3-azidopyrrolidine (2.02 g, 0.01 mole) in 30 ml of 98% ethanol was added 15 ml of butyne and heated in a sealed steel reaction vessel at 105°-110° C. for 24 hr. Removal of the solvent under reduced pressure afforded 2.55 g of the crude which contained 50% starting material. Chromatography over silica gel using hexane/ethyl acetate (1:1) as solvent yielded 0.88 g of the desired product. 1H NMR (CDCl3) δ: 7.36-7.2 (m, 5H), 4.95-4.8 (m, 1H), 3.7 (S, 2H), 3.2-3.1 (m, 1H), 2.93-2.76 (m, 3H), 2.48-2.3 (m, 2H), 2.24 (s, 3H), 2.21 (s, 3H).

Provenance & Evidence