Triacetoxyperiodinane → HCID 118005538, compound

HRID 926535Notes

Reaction equation

HRID 926535 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:38]1[CH:39]=[N:40][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:43]=1)[CH:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1>C(Cl)Cl>[F:47][C:44]([F:45])([F:46])[C:41]1[CH:42]=[CH:43][C:38]([C:24]([CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:29][CH2:30]2)=[O:23])=[CH:39][N:40]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118005515HCID 118005515, compound

Product 1

HCID 118005538HCID 118005538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dess-Martin periodinane reagent (30.0 g, 70.8 mmol) was added to a solution of tert-butyl 4-(hydroxy(6-(trifluoromethyl)pyridin-3-yl)methyl)piperidine-1-carboxylate (Intermediate 56: step a, 17.8 g, 49.5 mmol) in DCM (354 mL) at room temperature and the mixture was stirred for 2 hours. The reaction mixture was diluted with DCM and washed with saturated aqueous solution of NaHCO3. The organic phase was dried (MgSO4), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes) to provide the title compound that was 90% pure by NMR and was carried on to the next step.

Workup

  1. washwashed with saturated aqueous solution of NaHCO3
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-9158f689f719433680dc89e37af2e329
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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