Methanesulfonic Acid → (R)-1-(5-bromopyridin-2-yl)-2-hydroxylpropan-1-one

HRID 1483164Notes

Reaction equation

HRID 1483164 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[C@H:9]([O:11]C2CCCCO2)[CH3:10])=[N:6][CH:7]=1.CS(O)(=O)=O>C(O)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[C@H:9]([OH:11])[CH3:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 90266360(2R)-1-(5-bromopyridin-2-yl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

Product 1

HCID 90266361(R)-1-(5-bromopyridin-2-yl)-2-hydroxylpropan-1-oneYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Compound 1a (4.0 g, 12.7 mmol) was dissolved in isopropanol (50 mL), and methylsulfonic acid (1.8 g, 18.5 mmol) was added. The reaction was agitated at room temperature for 5 hrs. The reaction was monitored by TLC (petroleum ether/ethyl acetate=5/1). After the reaction completed, the solvent and excess methylsulfonic acid was removed by evaporation. The mixture was then diluted with water. The pH value was adjusted to 7-8 with saturated NaHCO3 solution. The mixture was extracted by ethyl acetate (30 mL×2). The organic phase was combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then dried by rotary dryer. Column chromatography (petroleum ether/ethyl acetate=7/1) afforded 1.6 g of white solid (compound 1b), yield 55%.

Workup

  1. customthe solvent and excess methylsulfonic acid was removed by evaporation
  2. additionThe mixture was then diluted with water
  3. extractionThe mixture was extracted by ethyl acetate (30 mL×2)
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customdried by rotary dryer

Sources & evidence

ORD record
ord-3bf5418eda264b7dbfb5b5d9e2e3592f
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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