Triacetoxyperiodinane → HCID 118005538, compound

HRID 1478497Notes

Reaction equation

HRID 1478497 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 14: step a, 17.8 g, 49.5 mmol) in DCM 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. 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
  5. customThe crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-dee49056aaec4cbea110021cb4fd7359
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

Loading…