Ammonium formate → HCID 67339702, compound

HRID 1675077Notes

Reaction equation

HRID 1675077 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67339781HCID 67339781, compound

Product 1

HCID 67339702HCID 67339702, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole-5-carboxylate (5.0 g, 14.03 mmol), ammonium formate (4.42 g, 70.14 mmol) and palladium (5% on activated carbon, 200 mg) in ethanol (80 mL) were stirred and refluxed for 1 hour. The resulting mixture was cooled to ambient temperature and filtered through diatomaceous earth. The filtrate was concentrated by evaporation then treated with dilute aqueous ammonium chloride (100 mL) and extracted with ethyl acetate. The extract was washed sequentially with water and saturated brine, dried over MgSO4 and evaporated to a colourless solid. The solid was triturated with ether, then collected by filtration and air dried to give methyl 3-[1-(tert-butoxycarbonyl)piperidin-4-yl]-1H-indole-5-carboxylate (4.59 g, 91%) as a colourless solid.

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated by evaporation
  4. additionthen treated with dilute aqueous ammonium chloride (100 mL)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed sequentially with water and saturated brine
  7. dry with materialdried over MgSO4
  8. customevaporated to a colourless solid
  9. customThe solid was triturated with ether
  10. filtrationcollected by filtration and air
  11. customdried

Sources & evidence

ORD record
ord-a1cd93c9f0b848fd8ccbf839c85d1d2d
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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