Triacetoxyperiodinane → HCID 86622382, compound

HRID 1864763Notes

Reaction equation

HRID 1864763 reaction equation
[C:1]([N:4]1[C:8]([CH2:15][CH2:16][CH2:17][OH:18])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6]([C:19]2[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=2[F:26])=[N:5]1)(=[O:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([N:4]1[C@:8]([CH2:15][CH2:16][CH:17]=[O:18])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:7][C:6]([C:19]2[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:20]=2[F:26])=[N:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69019214HCID 69019214, compound

Product 1

HCID 86622382HCID 86622382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 180 mg (0.429 mmol) 3-5 in 2.0 mL DCM at RT under N2 was added 218 mg (0.515 mmol) Dess-Martin Periodinane. After stirring for 30 min, the reaction was quenched by slowly adding saturated aqueous Na2SO3 solution followed by saturated aqueous NaHCO3 solution. The mixture stirred for 15 min before it was poured into EtOAc and separated. The organic phase was washed with 1:1 saturated aqueous Na2SO3-saturated aqueous NaHCO3 solution, water, brine, then dried with Na2SO4 and concentrated to yield 3-6 as a white foam.

Workup

  1. customthe reaction was quenched by slowly adding saturated aqueous Na2SO3 solution
  2. stirringThe mixture stirred for 15 min before it
  3. additionwas poured into EtOAc
  4. customseparated
  5. washThe organic phase was washed with 1:1 saturated aqueous Na2SO3-saturated aqueous NaHCO3 solution, water, brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fcaeb57a0ba543efbe566c7ad3dd3a82
Source dataset
uspto-grants-2009_12
Patent number
US07625936B2

Reaction notes

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