Ammonium formate → HCID 15639097, compound

HRID 21383Notes

Reaction equation

HRID 21383 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-68a0f8e7a130458f945f13281e7fb573
Source dataset
uspto-grants-1995_06
Patent number
US05422354

Reaction notes

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