Acetic Anhydride → Efppea

HRID 2389934Notes

Reaction equation

HRID 2389934 reaction equation
[CH2:1]([C:3]1[C:14]([CH2:15][CH2:16][NH2:17])=[C:6]2[C:7]3[CH2:13][CH2:12][O:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([C:3]1[C:14]([CH2:15][CH2:16][NH:17][C:25](=[O:27])[CH3:26])=[C:6]2[C:7]3[CH2:13][CH2:12][O:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 533089832-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine

Product 1

HCID 24954989EfppeaYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine (110 mg, 0.476 mmol) and triethylamine (133 μL, 0.954 mmol) in tetrahydrofuran (5 mL) was added acetic anhydride (90.0 μL, 0.952 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. A saturated aqueous sodium hydrogen carbonate solution (50 μL) was added to the reaction solution, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=90/10→100/0) and recrystallization (ethyl acetate/diisopropyl ether) to give the title compound (67.8 mg, yield 52%).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=90/10→100/0) and recrystallization (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-52c529b7babf419fac0866367521e7f0
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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