Benzene → N-benzyl-3-(5-ethoxycarbonyl-1,2,3-triazol-1-yl) pyrrolidine

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Reaction Steps

A mixture of N-benzyl-3-azido-pyrrolidine (5 g, 0.024 mmol) and ethylpropiolate (5 g, 0.051 mmol) in benzene (50 ml) heated under reflux for 48 hrs. Reaction solution was evaporated to dark brown oil, purified on silica gel column using ethylacetate, CHCl3 and methanol to get N-benzyl-3-(5-ethoxycarbonyl-1,2,3-triazol-1-yl) pyrrolidine (1.5 g, 20.6%). 1H NMR (CDCl3) δ: 1.37 (t, 3H), 2.42-2.58 (m, 2H), 2.71-3.01 (m, 3H), 3.20-3.32 (m, 1H), 3.73 (S, 2H), 4.35 (q, 2H), 5.72-5.88 (m, 1H), 7.2-7.4 (m, 5H), 8.12 (S, 1H). N-benzyl-3-(4-ethoxy carbonyl -1,2,3-triazol-1-yl)pyrrolidine (5 g, 68.7%). 1H NMR (CDCl3) δ: 1.40 (t, 3H), 1.8-3.20 (m, 6H), 3.70 (S, 2H), 4.40 (q, 2H), 5.06-5.48 (m, 1H), 7.33 (S, 5H), 8.43 (S, 1H).

Provenance & Evidence