1-Butyne → N-Benzyl-3-(4,5-dimethyl-1,2,3-triazol-1-yl)pyrrolidine

HRID 1742992Notes

Reaction equation

HRID 1742992 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.[CH:16]#[C:17][CH2:18][CH3:19]>C(O)C.CCCCCC.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[C:18]([CH3:19])=[C:17]([CH3:16])[N:15]=[N:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 78461-ButyneHCID 114242213-Azido-1-benzylpyrrolidine

Product 1

HCID 19006027N-Benzyl-3-(4,5-dimethyl-1,2,3-triazol-1-yl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of N-benzyl-3-azidopyrrolidine (2.02 g, 0.01 mole) in 30 ml of 98% ethanol was added 15 ml of butyne and heated in a sealed steel reaction vessel at 105°-110° C. for 24 hr. Removal of the solvent under reduced pressure afforded 2.55 g of the crude which contained 50% starting material. Chromatography over silica gel using hexane/ethyl acetate (1:1) as solvent yielded 0.88 g of the desired product. 1H NMR (CDCl3) δ: 7.36-7.2 (m, 5H), 4.95-4.8 (m, 1H), 3.7 (S, 2H), 3.2-3.1 (m, 1H), 2.93-2.76 (m, 3H), 2.48-2.3 (m, 2H), 2.24 (s, 3H), 2.21 (s, 3H).

Workup

  1. customRemoval of the solvent under reduced pressure
  2. customafforded 2.55 g of the crude which

Sources & evidence

ORD record
ord-5afe8ec706cc428a881798c7728143e9
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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