Triacetoxyperiodinane → HCID 58123994, compound

HRID 536657Notes

Reaction equation

HRID 536657 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([N:30]1[CH2:37][CH2:36][CH:35]2[CH2:38][CH:31]1[CH2:32][CH2:33][CH:34]2[OH:39])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:23]([N:30]1[CH2:37][CH2:36][CH:35]2[CH2:38][CH:31]1[CH2:32][CH2:33][C:34]2=[O:39])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58123729HCID 58123729, compound

Product 1

HCID 58123994HCID 58123994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.30 g) is added to a solution of 2-benzyl-2-aza-bicyclo[3.3.1]-nonan-6-ol (0.60 g) in dichloromethane (15 mL) chilled in an ice bath. The cooling bath is removed and the solution is stirred at ambient temperature for 1 h. Then, the solution is diluted with dichloromethane and washed with a mixture of aqueous Na2S2O3 solution and aqueous NaHCO3 solution. The solution is dried (Na2SO4) and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->2:1).

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionThen, the solution is diluted with dichloromethane
  4. washwashed with a mixture of aqueous Na2S2O3 solution and aqueous NaHCO3 solution
  5. dry with materialThe solution is dried (Na2SO4)
  6. customthe solvent is removed
  7. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->2:1)

Sources & evidence

ORD record
ord-5352bb6396004457b3a4df71d13b6536
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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