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

Reaktionsgleichung

[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]=[N+:14]=[N-:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C:18]#[C:19][C:20]([O-:22])=[O:21])C.[CH:23]1C=CC=C[CH:24]=1>>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:15]=[N:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Edukt 3

HCID 241Benzene

HCID 114242213-Azido-1-benzylpyrrolidine

HCID 22377350ETHYLPropiolate

Produkt 1

HCID 19006033N-benzyl-3-(5-ethoxycarbonyl-1,2,3-triazol-1-yl) pyrrolidineAusbeute 20,6 %

Versuchsvorschrift

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).