Triacetoxyperiodinane → HCID 178520961, compound

HRID 2368158Notes

Reaction equation

HRID 2368158 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[CH2:17][CH2:16]2)[CH:10]=3)[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH:21]=[O:22])[CH2:17][CH2:16]2)[CH:10]=3)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178520962HCID 178520962, compound

Product 1

HCID 178520961HCID 178520961, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of {trans-4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]cyclohexyl}methanol (3.50 g) in acetonitrile (100 mL) was added Dess-Martin reagent (5.93 g), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (3.30 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-84e042e00e304850a119da59c696d8a0
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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