Sulfuric Acid → HCID 66874574, compound

HRID 1799666Notes

Reaction equation

HRID 1799666 reaction equation
B.O1CCCC1.[CH3:7][O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=O)[N:18]([CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO>[CH3:7][O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 66874566HCID 66874566, compound

Product 1

HCID 66874574HCID 66874574, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 3.09 mL, 3.09 mmol) was added at 0° C. to a solution of 8-(methyl-phenyl-carbamoyl)-octanoic acid methyl ester (300 mg, 1.03 mmol) in tetrahydrofuran (20 mL) The reaction mixture was stirred at room temperature overnight. A further aliquot of borane-tetrahydrofuran complex (2.1 mL, 2.1 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. Methanol (60 mL) was added followed by concentrated sulfuric acid. The reaction mixture was refluxed at 80° C. for 2 hours. After cooling to room temperature, saturated sodium carbonate was added and the reaction mixture was extracted 3 times with dichloromethane. The combined organic layers were dried over sodium sulfphate, filtered and the solvent was removed in vacuo. The crude product was purified by chromatography (SiO2; heptane-ethyl acetate gradient) to afford 9-(methyl-phenyl-amino)-nonanoic acid methyl ester (89 mg, 31%).

Workup

  1. additionA further aliquot of borane-tetrahydrofuran complex (2.1 mL, 2.1 mmol) was added
  2. stirringthe reaction mixture was stirred at room temperature for 3.5 hours
  3. temperatureThe reaction mixture was refluxed at 80° C. for 2 hours
  4. temperatureAfter cooling to room temperature
  5. extractionthe reaction mixture was extracted 3 times with dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfphate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe crude product was purified by chromatography (SiO2; heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-ad8c632edcca4d338154e0efcc8a7df3
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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