Methanol → HCID 57522146, compound

HRID 554203

Reaction equation

HRID 554203 reaction equation
[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([CH:12]=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][NH2:15].[BH4-].[Na+].[OH2:18].[CH3:19][OH:20]>[Cl-].[Na+].O>[CH3:14][N:15]([CH2:12][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][CH:10]=1)[C:19](=[O:20])[O:18][C:1]([CH3:7])([CH3:6])[CH3:2]

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 110520905-Phenyl-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 57522146HCID 57522146, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (92 mL) of 5-phenyl-1H-pyrrole-3-carbaldehyde (0.92 g) in methanol was added 40% methylamine solution (1.26 g) at room temperature and the mixture was stirred for 30 min. To the reaction mixture was added sodium borohydride (305 mg) at room temperature and the mixture was stirred for 10 min. Water (200 mL) was added and the mixture was further stirred for 1 hr. Saturated brine (50 mL) 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 acetonitrile (48 mL), and di-tert-butyl bicarbonate (1.41 g) was added dropwise at room temperature. The mixture was stirred for 1.5 hr and partitioned with water and ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as colorless crystals (yield 0.99 g, 64%).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in acetonitrile (48 mL)
  8. additiondi-tert-butyl bicarbonate (1.41 g) was added dropwise at room temperature
  9. stirringThe mixture was stirred for 1.5 hr
  10. custompartitioned with water and ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-ac3ca403bcfe44e396a957ac40052656
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Linked notes

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