Triacetoxyperiodinane → HCID 71205433, compound

HRID 2280868Notes

Reaction equation

HRID 2280868 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:7]=[N:8][CH:9]=[C:10]([CH:15]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:5][N:4]([C:6]2[CH:7]=[N:8][CH:9]=[C:10]([CH:15]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71205429HCID 71205429, compound

Product 1

HCID 71205433HCID 71205433, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 11a (250 mg, 1.20 mmol) in dry DCM (15 mL) was added Dess-Martin periodinane (1.014 g, 2.40 mmol) at 0° C. under N2 atmosphere and the solution was stirred at rt for 2 h. The resulting solution was quenched with saturated sodium bicarbonate solution and diluted with EA. The organic portion was washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure and purified by CC (DCM/MeOH=150:1) to give compound 11 (140 mg, 57%) of as a yellow solid.

Workup

  1. customThe resulting solution was quenched with saturated sodium bicarbonate solution
  2. additiondiluted with EA
  3. washThe organic portion was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by CC (DCM/MeOH=150:1)

Sources & evidence

ORD record
ord-e3f649c72a244c00abff216e8047bc32
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

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