Ammonium formate → 3-Phenyl-8-azabicyclo[3.2.1]octan-3-ol

HRID 238258Notes

Reaction equation

HRID 238258 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]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:16])[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>O.[OH-].[OH-].[Pd+2]>[C:17]1([C:11]2([OH:16])[CH2:10][CH:9]3[NH:8][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 130912248-Benzyl-3-phenyl-8-azabicyclo[3.2.1]octan-3-ol

Product 1

HCID 130912463-Phenyl-8-azabicyclo[3.2.1]octan-3-olYield 76.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]octan-3-ol (0.24 g, 0.84 mmol) was dissolved in IMS (4.5 mL) and water (0.5 mL). Ammonium formate (0.5 g) and Pearlman's catalyst (0.12 g) were added. The mixture was heated to reflux for 0.5 hour, filtered and the solution concentrated to give an oil which was purified by chromatography on an SCX cartridge eluting with ammonia (2 M) in methanol. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.13 g) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 0.5 hour
  3. filtrationfiltered
  4. concentrationthe solution concentrated
  5. customto give an oil which
  6. customwas purified by chromatography on an SCX cartridge
  7. washeluting with ammonia (2 M) in methanol
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-085bc920ebf24bbea48f138f02e59d77
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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