Ethyl Acetate → (1R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one

HRID 2088099Notes

Reaction equation

HRID 2088099 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:10](=[O:25])[CH:11]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>CO.[OH-].[Pd+2].[OH-]>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:17])=[O:18])[CH2:15][C@@:9]1([C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[C:10](=[O:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69891746HCID 69891746, compound

Product 1

HCID 69889540(1R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-oneYield 84%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(1R*,5S*,6R*)-8-Benzyl-1-(4-fluorophenyl)-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-ene-2-one (Description 12; 13.88 g, 31.05 mmol) was dissolved in methanol (25 ml) and ethyl acetate (25 ml) and 10% palladium hydroxide (1.80 g) added and the mixture hydrogenated at 30 psi for 30 minutes. The mixture was filtered and concentrated in vacuo to give the title compound as a yellow oil (11.65 g, 84%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2c37584be73475c881ccb774d040341
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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