Ammonium formate → HCID 63969005, compound

HRID 2202785Notes

Reaction equation

HRID 2202785 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)([OH:16])[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>O.[Pd]>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[C:11]1([OH:16])[CH2:12][CH:13]2[NH:8][CH:9]([CH2:15][CH2:14]2)[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67466423HCID 67466423, compound

Product 1

HCID 63969005HCID 63969005, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

8-Benzyl-3-pyrazin-2-yl-8-aza-bicyclo[3.2.1]octan-3-ol (0.25 g, 0.85 mmol) was dissolved in IMS (10 mL) and water (1 mL). Palladium on carbon (10%; 0.1 g) was added under nitrogen. Ammonium formate (0.58 g, 9.2 mmol) was added and the mixture heated at reflux for 1 hour. The mixture was allowed to cool, filtered and the solvent removed by evaporation under vacuum. The residues were passed through an SCX cartridge, eluting with 2 M ammonia in methanol to give the title compound as a colourless oil (0.11 g). LCMS m/z 206.2 [M+H]+. R.T.=0.34 min (Analytical Method 3).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under vacuum
  6. washeluting with 2 M ammonia in methanol

Sources & evidence

ORD record
ord-c8ab93d1a4b74933af31745db928ec7a
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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