Sodium Carbonate → HCID 89854305, compound

HRID 931268Notes

Reaction equation

HRID 931268 reaction equation
[CH2:1]([N:8]([C@@H:19]([CH3:22])[CH2:20][OH:21])[CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:18])O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([N:8]1[C@@H:19]([CH3:22])[CH2:20][O:21][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=2[O-:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 89854038HCID 89854038, compound

Product 1

HCID 89854305HCID 89854305, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

2-(2-(Benzyl((S)-1-hydroxypropan-2-yl)amino)-1-hydroxyethyl)pyridine 1-oxide (7 g, 23.17 mmol) was dissolved in 70% sulfuric acid (70 mL) and the mixture was heated at reflux for 7 h. The mixture was cooled and then was diluted with water, neutralized with an aqueous sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by alumina chromatography (1% methanol in dichloromethane) to afford 2-((5S)-4-benzyl-5-methylmorpholin-2-yl)pyridine 1-oxide as a yellow liquid (3 g, 45%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 7 h
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by alumina chromatography (1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4b0fdc8102004e808f1e0ad639689c61
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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