Sodium borohydride → HCID 66925240, compound

HRID 554414Notes

Reaction equation

HRID 554414 reaction equation
[C:1]1([C:7]2[C:8]([CH:27]=O)=[CH:9][N:10]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[CH3:31][NH2:32].[BH4-].[Na+]>CO.O1CCCC1>[C:1]1([C:7]2[C:8]([CH2:27][NH:32][CH3:31])=[CH:9][N:10]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86232871HCID 86232871, compound

Product 1

HCID 66925240HCID 66925240, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4,5-Diphenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (202 mg) was dissolved in methanol (2 mL) and tetrahydrofuran (2 mL), 40% methylamine methanol solution (0.5 mL) was added at room temperature, and the mixture was stirred for 15 min. To the reaction mixture was added sodium borohydride (22 mg) at room temperature, and the mixture stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, to the residue was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate) to give the title compound as white crystals (yield 181 mg, 87%).

Workup

  1. stirringthe mixture stirred for 1 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  3. additionwas added saturated aqueous sodium hydrogencarbonate solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-89f0b32de6ad4ac98c4547cde9e3811f
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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