Ammonium formate → HCID 21830631, compound

HRID 1600898Notes

Reaction equation

HRID 1600898 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:30])[CH:22]=[CH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH:11]=[CH:10]2>[Pd].C(O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:30])[CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54307828HCID 54307828, compound

Product 1

HCID 21830631HCID 21830631, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ammonium formate (2.0 g), palladium on charcoal (10%; 0.5 g) and 5-(6-methoxy-2-naphthyl)ethyl-1-(3-pyridyl)-1-penten-3-one (0.7 g) in ethanol (50 ml) was heated at reflux for 5 minutes. The reaction mixture was then filtered through Celite and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (1:5) to give 5-(6methoxy-2-naphthyl)ethyl-1-(3-pyridyl)-3-pentanone (0.3 g). The latter (0.2 g) was dissolved in ethanol (20 ml) and solid sodium borohydride (0.1 g) was added over 10 minutes. The solution was concentrated under reduced pressure and the residue was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a solid (0.1 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 minutes
  3. filtrationThe reaction mixture was then filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica eluting with ethyl acetate:dichloromethane (1:5)

Sources & evidence

ORD record
ord-e32b03dc3f8a4ea29036e09b7b2c2ed0
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

Loading…