Sodium Bicarbonate → HCID 66925156, compound

HRID 554428Notes

Reaction equation

HRID 554428 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][C:15]([CH:24]=O)=[CH:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].Cl.[CH3:27][NH2:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>CO>[CH3:27][NH:28][CH2:24][C:15]1[CH:16]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]([S:10]([C:6]2[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=2)(=[O:12])=[O:11])[CH:14]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 86232861HCID 86232861, compound

Product 1

HCID 66925156HCID 66925156, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(3-Acetylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (200 mg) was dissolved in methanol (30 mL), methylamine hydrochloride (192 mg) was added at room temperature and the mixture was stirred for 30 min. Sodium triacetoxyborohydride (360 mg) was added at room temperature and the mixture was stirred for 2 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture 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: ethyl acetate-methanol=1:0→7:3), and dissolved in ethyl acetate (10 mL). Oxalic acid (50 mg) was added and the mixture was stirred for 15 min. The crystallized crystals were collected by filtration to give the title compound as colorless crystals (yield 6.7 mg, 3%).

Workup

  1. stirringthe mixture was stirred for 2 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. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→7:3)
  7. dissolutiondissolved in ethyl acetate (10 mL)
  8. additionOxalic acid (50 mg) was added
  9. stirringthe mixture was stirred for 15 min
  10. filtrationThe crystallized crystals were collected by filtration

Sources & evidence

ORD record
ord-35bc98dd810348a89b8ab6838dd6e48c
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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