Sodium borohydride → 2-Fluoro-2-methyl-1-(pyridin-3-yl)propan-1-ol
Reaction equation
[F:1][C:2]([CH3:12])([CH3:11])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[BH4-].[Na+]>CO>[F:1][C:2]([CH3:12])([CH3:11])[CH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In methanol (30.0 mL) was dissolved 2-fluoro-2-methyl-1-(pyridin-3-yl)propan-1-one (1.73 g, 10.3 mmol) obtained in Step 3. Sodium borohydride (584 mg, 15.4 mmol) was added and the mixture was stirred at 0° C. for 30 minutes. The solvent was evaporated under reduced pressure and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) and further purified by preparative thin-layer chromatography (hexane/ethyl acetate=3/7) to give Compound A11 (1.54 g, 89% yield).
Workup
- customThe solvent was evaporated under reduced pressure and water
- additionwas added
- extractionExtraction with ethyl acetate
- washwashing with saturated brine
- dry with materialdrying over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe solvent in the filtrate was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
- customfurther purified by preparative thin-layer chromatography (hexane/ethyl acetate=3/7)
- customto give Compound A11 (1.54 g, 89% yield)
Sources & evidence
- ORD record
- ord-f01bd0c2f5f84e6f989030d525ca9640
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150569B2
Reaction notes
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