Sodium Bicarbonate → HCID 22928670, compound

HRID 1453916Notes

Reaction equation

HRID 1453916 reaction equation
F[B-](F)(F)F.[CH3:6][O+:7]([CH3:9])C.[CH2:10]([CH:17]1[CH:21]([CH2:22][CH2:23][CH3:24])[CH2:20][NH:19]C1=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:6][O:7][C:9]1[CH:17]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:21]([CH2:22][CH2:23][CH3:24])[CH2:20][N:19]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 22928682HCID 22928682, compound

Product 1

HCID 22928670HCID 22928670, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyloxonium tetrafluoroborate (0.85 g, 5.7 mmol) was added to a solution of 3-benzyl-4-propyl-2-pyrrolidinone (0.83 g, 3.8 mmol) in methylene chloride (15 ml) and the mixture was stirred at room temperature for 14 hours. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture to render it weekly basic and then extraction was performed with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (0.67 g) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.75 (3H, t, J=7.2 Hz), 1.02-1.28 (4H, m), 2.02-2.16 (1H, m), 2.55-2.66 (1H, m), 2.69 (1H, dd, J=13.2 Hz, 8.4 Hz), 2.99 (1H, dd, J=13.2 Hz, 4.8 Hz), 3.10 (1H, dd, J=13.2 Hz, 5.2 Hz), 3.58 (1H, dd, J=13.2 Hz, 8.8 Hz), 3.83 (3H, s), 7.05-7.40 (5H, m)

Workup

  1. extractionextraction
  2. washAfter washing the organic layer with brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-aac663443d9c4b5c88eba9584407a10c
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Reaction notes

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