Phenethylamine → HCID 59741434, compound

HRID 554386Notes

Reaction equation

HRID 554386 reaction equation
[CH3:1][S:2]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH:16]=O)=[CH:6]1)(=[O:4])=[O:3].C([CH2:25][NH2:26])C1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][S:2]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:16][NH:26][CH3:25])=[CH:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86232916HCID 86232916, compound

Product 1

HCID 59741434HCID 59741434, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (5 mL) of 1-(methylsulfonyl)-5-phenyl-1H-pyrrole-3-carbaldehyde (160 mg) in tetrahydrofuran was added benzylmethylamine (117 mg), and the mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (435 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 (10 mL), 10% palladium carbon (50% water-containing product, 200 mg) and 1 mol/l hydrochloric acid (1 mL) were added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 18 hr. The reaction mixture was filtrated; and the filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added to the residue, 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→ethyl acetate) to give the title compound as a colorless oil (yield 62 mg, 37%).

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 (10 mL)
  7. addition10% palladium carbon (50% water-containing product, 200 mg) and 1 mol/l hydrochloric acid (1 mL) were added
  8. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 18 hr
  9. filtrationThe reaction mixture was filtrated
  10. concentrationand the filtrate was concentrated under reduced pressure
  11. additionSaturated aqueous sodium hydrogen carbonate was added to the residue
  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→ethyl acetate)

Sources & evidence

ORD record
ord-9fdf9fc0d62f4866b6691ca7bcc026df
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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