Phenethylamine → HCID 66924642, compound

HRID 554385Notes

Reaction equation

HRID 554385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH:22]=O)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([CH2:31][NH2:32])C1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:22][NH:32][CH3:31])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86232912HCID 86232912, compound

Product 1

HCID 66924642HCID 66924642, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (5 mL) of 1-[(4-fluorophenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (160 mg) in tetrahydrofuran was added benzylmethylamine (88 mg), and the mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (329 mg) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in methanol (5 mL), 10% palladium carbon (50% water-containing product, 180 mg) and formic acid (0.027 mL) were added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 10 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→2:1) to give the title compound as a colorless oil (yield 55 mg, 33%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in methanol (5 mL)
  7. addition10% palladium carbon (50% water-containing product, 180 mg) and formic acid (0.027 mL) were added
  8. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 10 hr
  9. filtrationThe reaction mixture was filtrated
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. additionTo the residue was added saturated aqueous sodium hydrogen carbonate
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe extract was washed with saturated brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→2:1)

Sources & evidence

ORD record
ord-22d7f140329746c4854fd99c2f21e2ec
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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