3,5-Dimethoxybenzaldehyde → N-(5-((1R,2S)-2-(3,5-Dimethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 218113Notes

Reaction equation

HRID 218113 reaction equation
[NH2:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1)[CH:23]=O>CO>[CH3:29][O:28][C:26]1[CH:25]=[C:22]([CH:21]=[C:20]([O:19][CH3:18])[CH:27]=1)[CH2:23][NH:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4]

Participants

4

Reactant 2

HCID 817473,5-DimethoxybenzaldehydeHCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 58280637N-(5-((1R,2S)-2-(3,5-Dimethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamideYield 57.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Borane-pyridine complex (445 μL, 4.18 mmol) was added to a methanol solution (10 mL) of an amine (3) (363 mg, 1.39 mmol) and 3,5-dimethoxybenzaldehyde (301 mg, 1.81 mmol), and the mixture was stirred for two hours. The reaction mixture was allowed to cool to room temperature and extracted after addition of water with a mixed solvent (ethyl acetate: methanol=10:1), and the organic layer was washed with saturated aqueous sodium chloride solution. The organic layer was dried and concentrated, and the crude product obtained was purified by amine silica gel column chromatography (eluant:chloroform:methanol=7:1), to give a desired amine (4) as a pale yellow solid (329 mg, yield: 57%).

Workup

  1. extractionextracted
  2. additionafter addition of water with a mixed solvent (ethyl acetate: methanol=10:1)
  3. washthe organic layer was washed with saturated aqueous sodium chloride solution
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe crude product obtained
  7. customwas purified by amine silica gel column chromatography (eluant:chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-deeeaaa7ccd3464d9838369853cbd442
Source dataset
uspto-grants-2012_06
Patent number
US08198330B2

Reaction notes

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