Acetylene → Rac-tert-butyl (3r,4r)-3-hydroxy-4-(1h-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of trans 3-hydroxy-4-azido-1-N-(tert.-butoxy carbonyl)pyrrolidine (3.8 g, 17 mmol) in dry acetone (50 ml) was heated at 75°-80° C. for 40 hrs. After releasing the excess of acetylene, the reaction mixture was concentrated and the residue was purified on silica gel using ethyl acetate as eluant. Yield 3.66 g (87%) m.p. 91-93° C.; 1H NMR (CDCl3) δ: 1.46 (S, 9H), 3.25-4.25 (m, 5H), 4.83 (m, 1H), 7.63 (S, 1H), 7.70 (S, 1H).

Provenance & Evidence