Triacetoxyperiodinane → HCID 71226974, compound

HRID 2409889Notes

Reaction equation

HRID 2409889 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH2:11]1)[C:5]#[N:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 56828410HCID 56828410, compound

Product 1

HCID 71226974HCID 71226974, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-fluoro-4-(3-hydroxypiperidin-1-yl)benzonitrile (2.4 g, 10.90 mmol) in CH2Cl2 (50 mL) was added Dess-Martin Periodinane (6.93 g, 16.35 mmol). The reaction was stirred at rt for 1 h. The reaction was then diluted with CH2Cl2, washed with aqueous 10% Na2S2O3, saturated aqueous Na2CO3 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, 3-fluoro-4-(3-oxopiperidin-1-yl)benzonitrile, (730 mg, 3.35 mmol, 30.7% yield) as a white foam. Anal. Calcd. for C12H11FN2O m/z 218.2, found: 219.1 (M+H)+.

Workup

  1. washwashed with aqueous 10% Na2S2O3, saturated aqueous Na2CO3 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-26387314e6b74b1baedf6f83ff7ca731
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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