Triacetoxyperiodinane → HCID 86664524, compound

HRID 1028444Notes

Reaction equation

HRID 1028444 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]([C:27]1[CH:28]=[C:29]([CH2:66][OH:67])[C:30]([O:64][CH3:65])=[C:31]([NH:33][C:34]([C:36]2[CH:37]=[CH:38][C:39]([CH3:63])=[C:40]([CH:62]=2)[O:41][C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH2:48][CH:49]3[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]3)[CH:43]=2)=[O:35])[CH:32]=1)([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([C:27]1[CH:28]=[C:29]([CH:66]=[O:67])[C:30]([O:64][CH3:65])=[C:31]([NH:33][C:34]([C:36]2[CH:37]=[CH:38][C:39]([CH3:63])=[C:40]([CH:62]=2)[O:41][C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH2:48][CH:49]3[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:56])[CH2:51][CH2:50]3)[CH:43]=2)=[O:35])[CH:32]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67491419HCID 67491419, compound

Product 1

HCID 86664524HCID 86664524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

120 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (“Dess-Martin-Periodinane”) are added to an ice-cooled solution of 200 mg of tert-butyl 4-{4-[5-(5-tert-butyl-3-hydroxymethyl-2-methoxy-phenylcarbamoyl)-2-methyl-phenoxy]-pyridin-2-ylmethyl}-piperidine-1-carboxylate in 6 ml dichloromethane. The cooling bath is removed, and the solution is stirred overnight at ambient temperature. Then the solution is diluted with dichloromethane and washed with aqueous K2CO3 solution and aqueous Na2S2O3 solution. The organic phase is dried (Na2SO4) and the solvent is removed. The residue is chromatographed on silica gel with dichloromethane/methanol (99:1→90:10) as eluant.

Workup

  1. customThe cooling bath is removed
  2. additionThen the solution is diluted with dichloromethane
  3. washwashed with aqueous K2CO3 solution and aqueous Na2S2O3 solution
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. customthe solvent is removed
  6. customThe residue is chromatographed on silica gel with dichloromethane/methanol (99:1→90:10) as eluant

Sources & evidence

ORD record
ord-3cc55bb5c42c430986ea11a56d5e0046
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

Loading…