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

反応式

[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

参加物

反応物 3

HCID 241Benzene

HCID 114242213-Azido-1-benzylpyrrolidine

HCID 22377350ETHYLPropiolate

生成物 1

HCID 19006033N-benzyl-3-(5-ethoxycarbonyl-1,2,3-triazol-1-yl) pyrrolidine収率 20.6%

実験手順

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).