Ammonium formate → HCID 67339423, compound

HRID 1675018Notes

Reaction equation

HRID 1675018 reaction equation
[OH:1][C:2]1([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=2)[CH2:7][CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:27][C:24]([F:25])([F:26])[C:22]1[CH:23]=[C:18]([C:2]2([OH:1])[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]2)[CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67340546HCID 67340546, compound

Product 1

HCID 67339423HCID 67339423, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-hydroxy-4-[5-(trifluoromethyl)pyridin-3-yl]piperidine-1-carboxylate (1.30 g, 3.42 mmol), 5% palladium on activated carbon (50 mg) and ammonium formate (2.0 g) in ethanol (20 mL) were stirred and heated under reflux for 1 hour then cooled to ambient temperature and filtered through diatomaceous earth. The filtrate was applied to an SCX column and eluted with methanol followed by 2M ammonia in methanol. Fractions containing product were combined and evaporated then purified by flash silica chromatography, elution gradient 10 to 20% 2M ammonia in methanol in DCM. Pure fractions were evaporated to dryness to afford 4-[5-(trifluoromethyl)pyridin-3-yl]piperidin-4-ol (0.417 g, 50%) as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. filtrationfiltered through diatomaceous earth
  4. washeluted with methanol
  5. additionFractions containing product
  6. customevaporated
  7. customthen purified by flash silica chromatography, elution gradient 10 to 20% 2M ammonia in methanol in DCM
  8. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-198ec4592e4d4489be5bd7a7a7c3fbda
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

Loading…