Acetic Acid → 5H-Pyrrolo[1,2-a]imidazol-7-ol,6,7-dihydro-(9CI)

HRID 1398517Notes

Reaction equation

HRID 1398517 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)(=O)C.[CH:10]([CH:12]=[CH2:13])=[O:11]>O1CCOCC1>[N:1]1[CH:5]=[CH:4][N:3]2[CH2:13][CH2:12][CH:10]([OH:11])[C:2]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 795ImidazoleHCID 7847Acrolein

Product 1

HCID 138098115H-Pyrrolo[1,2-a]imidazol-7-ol,6,7-dihydro-(9CI)

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of imidazole (2 mL, 30.26 mmol) and acetic acid (0.12 mL, 2.12 mmol) in dry dioxane (20 mL) under N2 was added acrolein (3.03 mL, 45.39 mmol) in 1 portion and the resultant solution heated to reflux for 4 hr. The reaction mixture was concentrated in vacuo and the yellow-brown residue was purified by column chromatography, (elution with 25% methanol in DCM) to give the title product; 1H NMR (500 MHz, DMSO) delta 2.25 (1H, ddt, J=13.06, 7.90, 3.94, 3.94 Hz), 2.70-2.87 (1H, m), 3.85 (1H, ddd, J=10.72, 8.51, 4.26 Hz), 4.03 (1H, ddd, J=10.72, 7.80, 6.23 Hz), 4.86 (1H, dd, J=7.09, 3.00 Hz), 5.58 (1H, br. s.), 6.94 (1H, s), 7.06 (1H, d, J=0.95 Hz); LC-MS: m/z=+124.9 (M+H)+.

Workup

  1. temperatureto reflux for 4 hr
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe yellow-brown residue was purified by column chromatography, (elution with 25% methanol in DCM)

Sources & evidence

ORD record
ord-481c35cebcc840e4ab1fe5902ccdc82f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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