Acetone → N-Benzhydryl-3-(1,2,3-triazol-1-yl) azetidine

Participants

Reaction Steps

To a solution of 1.05 g (3.98 mmol) of N-benzhydryl-3-azidoazetidine in 50 ml of acetone cooled to -78° C. in a steel reaction vessel was bubbled 36 g of acetylene. The sealed reaction vessel after warming up to room temperature was heated at 80° C. for 17 hr. The solution was then cooled to room temperature, filtered and evaporated to yield the crude product which after chromatography over silica gel (2.5% methanol chloroform) yielded 0.88 g (76%) of the desired product as a solid, m.p. 167°-168° C. 1H NMR (CDCl3) δ: 7.88 (S, 1H), 7.73 (S, 1H), 7.55-7.07 (m, 10H), 5.35-5.1 (m, 1H), 4.53 (S, 1H), 3.76 (t, 2H), 3.5 (t, 2H).

Provenance & Evidence