Triacetoxyperiodinane → HCID 71226982, compound

HRID 2409890Notes

Reaction equation

HRID 2409890 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH2:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71227159HCID 71227159, compound

Product 1

HCID 71226982HCID 71226982, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluoro-4-(3-hydroxypiperidin-1-yl)benzonitrile (1,000 mg, 4.54 mmol) in CH2Cl2 (2 mL) was added Dess-Martin Periodinane (231 mg, 0.545 mmol). The reaction was stirred at rt for 1 h. The reaction was diluted CH2Cl2, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-50% EtOAc/Hex to give the product, 2-fluoro-4-(3-oxopiperidin-1-yl)benzonitrile, (600 mg, 2.75 mmol, 60.6% yield) as a white foam. Anal. Calcd. for C12H11FN2O m/z 218.2, found: 219.1 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 and saturated aqueous NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified
  6. washeluting with a gradient of 0-50% EtOAc/Hex

Sources & evidence

ORD record
ord-0c9b0003fae041ff823367ea5ff787b4
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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