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

HRID 1742999Notes

Reaction equation

HRID 1742999 reaction equation
[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

Participants

4

Reactant 3

HCID 241BenzeneHCID 114242213-Azido-1-benzylpyrrolidineHCID 22377350ETHYLPropiolate

Product 1

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

Procedure

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).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 hrs
  3. customReaction solution
  4. customwas evaporated to dark brown oil
  5. custompurified on silica gel column

Sources & evidence

ORD record
ord-5cb3d87b81b84440af495f4641fd5fd5
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

Loading…