(1R*,5S*,6R*)-8-Benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]oct-3-ene-2-one → (1R*,5S*,6R*)-8-Benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-one

HRID 1267897Notes

Reaction equation

HRID 1267897 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]#[N:17])[CH2:15][C@@:9]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:18])[CH:11]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[OH-].[Pd+2].[OH-]>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]#[N:17])[CH2:15][C@@:9]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:18])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69684828(1R*,5S*,6R*)-8-Benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]oct-3-ene-2-one

Product 1

HCID 69684638(1R*,5S*,6R*)-8-Benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-oneYield 96.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Palladium hydroxide (20%) (700 mg) was added to a solution of (1R*,5S*,6R*)-8-benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]oct-3-ene-2-one (Description 29; 7.1 g, 22.6 mmol) in methanol (100 ml). The mixture was transferred to the Parr™ apparatus and hydrogenated at 45 psi for 20 minutes. The mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate and brine. The organic layer was separated, dried (MgSO4), filtered and concentrated to yield the title compound (6.9 g, 96%).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and brine
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b877d0fa034fe1bbd428ed0b2a30b9
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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