Pyridine → HCID 17842560, compound

HRID 546450Notes

Reaction equation

HRID 546450 reaction equation
N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][C:32](O)([C:35]#[C:36][C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])O.[Na+]>ClCCl>[C:22]([O:26][C:27]([N:29]1[CH2:30][CH:31]=[C:32]([C:35]#[C:36][C:37]([O:39][CH3:40])=[O:38])[CH2:33][CH2:34]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 17842518HCID 17842518, compound

Product 1

HCID 17842560HCID 17842560, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (1.12 ml) and trifluoromethanesulfonic anhydride (875 μl) were added dropwise to a solution of 1-(tert-butoxycarbonyl)-4-hydroxy-4-(methoxycarbonyl-ethynyl)piperidine (490 mg) in dichloromethane (15 ml) at −78° C. After heating the mixture to room temperature in 1 hour, a saturated aqueous solution (50 ml) of sodium hydrogencarbonate and dichloromethane (10 ml) were added to the reaction mixture to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1→2:1) to obtain the title compound (249 mg) as a pale yellow oil.

Workup

  1. customto separate an organic layer
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1→2:1)

Sources & evidence

ORD record
ord-da3827ff78bb498a808879f3243ce959
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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