8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-ene → 3-Phenyl-8-azabicyclo[3.2.1]octane

HRID 238271Notes

Reaction equation

HRID 238271 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>O.[OH-].[OH-].[Pd+2]>[C:16]1([CH:11]2[CH2:10][CH:9]3[NH:8][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 4345538-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-eneHCID 2723923Ammonium formate

Product 1

HCID 249041703-Phenyl-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-ene (0.1 g) was dissolved in IMS (5 mL) and water (0.5 mL). Ammonium formate (0.21 g) and Pearlman's catalyst (0.02 g) were added and the mixture heated to 90° C. for 1 hour. After cooling, the mixture was filtered and concentrated under vacuum. The residue was purified on an SCX cartridge, eluting with aqueous ammonia (2 M) and methanol. The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil. LCMS m/z 188.4 [M+H]+. R.T.=2.22 min (Analytical Method 4).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on an SCX cartridge
  5. washeluting with aqueous ammonia (2 M) and methanol
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-f246abf319eb43988563349e596a1218
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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