Trifluoroacetic acid → HCID 57904713, compound

HRID 1021226Notes

Reaction equation

HRID 1021226 reaction equation
CS([O:5][CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)(=O)=O.[CH3:19][C:20]1[C:25](O)=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(C(F)(F)F)=O>ClCCCl.CN(C=O)C>[CH3:19][C:20]1[C:25]([O:5][CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 707192-Methylpyridin-3-olHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 57904713HCID 57904713, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (1.1 g), 2-methylpyridin-3-ol (500 mg), potassium carbonate (1.7 g), and DMF (10 ml) were mixed, followed by stirring at 100° C. for 6 hours. The reaction mixture was concentrated under reduced pressure, and CHCl3 and a saturated aqueous sodium hydrogen carbonate solution were then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH). The purified product thus obtained was mixed with DCE (10 ml), and TFA (4.5 g) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and CHCl3 and a 1 M aqueous NaOH solution were the added thereto, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure to obtain 2-methyl-3-(piperidin-4-yloxy)pyridine (355 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3
  2. additiona saturated aqueous sodium hydrogen carbonate solution were then added
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)
  6. customThe purified product thus obtained
  7. additionwas added
  8. stirringby stirring at room temperature for 3 hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3
  10. additionadded
  11. dry with materialthe organic layer was dried over Na2SO4
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bbc572ca597741c9a58affbca670f036
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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