Sodium borohydride → HCID 67403141, compound

HRID 1186346Notes

Reaction equation

HRID 1186346 reaction equation
[CH3:1][C:2]([CH3:15])([S:11]([CH3:14])(=[O:13])=[O:12])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[BH4-].[Na+]>CO>[CH3:14][S:11]([C:2]([CH3:15])([CH3:1])[CH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67402248HCID 67402248, compound

Product 1

HCID 67403141HCID 67403141, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[Dimethyl(methanesulfonyl)acetyl]pyridine (81.0 mg, 0.356 mmol) was dissolved in methanol (2.0 mL). To this, sodium borohydride (20.2 mg, 0.535 mmol) was added under a nitrogen atmosphere at 0° C. and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated, water was added thereto, and extraction with ethyl acetate was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol 9/1) to give 3-(2-methanesulfonyl-2-methyl-1-hydroxypropyl)pyridine (Compound CY) (86.7 mg, yield: quantitative).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionextraction with ethyl acetate
  4. dry with materialby drying over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol 9/1)

Sources & evidence

ORD record
ord-9ef331b8e73d4d72b9ea12f55d6c88ba
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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