Ammonium formate → HCID 15639097, compound

HRID 399441Notes

Reaction equation

HRID 399441 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:13][CH:12]2[N:14](CC3C=CC=CC=3)[CH:8]([CH2:9][CH2:10][CH2:11]2)[CH2:7]1)=[O:5])[CH3:2].C([O-])=O.[NH4+]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH:8]2[NH:14][CH:12]([CH2:11][CH2:10][CH2:9]2)[CH2:13]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 15639096Ethyl 9-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 15639097HCID 15639097, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 125 mL round-bottomed flask equipped with a condenser and N2 inlet were added 8.14 g (28.36 mmol) ethyl-N-benzyl-9-azabicyclo[3.3.1]nonane-3-carboxylate, 60 mL ethanol, 8.93 g (141.8 mmol) ammonium formate, and 5 g 10% palladium-on-carbon. The reaction was refluxed and fresh catalyst and ammonium formate were added until the starting material disappeared (about 4 hr, a total of 8 g catalyst). The reaction was cooled, filtered through diatomaceous earth (Celite [trademark]), and evaporated. The residue was partitioned between methylene chloride and an aqueous sodium hydroxide solution, and the organic layer separated, dried over sodium sulfate, and evaporated. The resulting oil was used directly in the next step.

Workup

  1. customTo a 125 mL round-bottomed flask equipped with a condenser and N2 inlet
  2. temperatureThe reaction was refluxed
  3. customabout 4 hr
  4. temperatureThe reaction was cooled
  5. filtrationfiltered through diatomaceous earth (Celite [trademark])
  6. customevaporated
  7. customThe residue was partitioned between methylene chloride
  8. customan aqueous sodium hydroxide solution, and the organic layer separated
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-9761cacec5f24914a914c81a09492919
Source dataset
uspto-grants-1998_10
Patent number
US05821248

Reaction notes

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