(6R*,9aS*)-6-(3-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one → (6R*,9aS*)-6-(3-fluorophenyl)octahydroquinolizin-4-one

HRID 553905Notes

Reaction equation

HRID 553905 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:17][CH2:16][CH2:15][C@@H:14]3[N:9]2[C:10](=[O:18])[CH2:11][CH:12]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.[H][H]>CO.[Pt]=O>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:17][CH2:16][CH2:15][C@@H:14]3[N:9]2[C:10](=[O:18])[CH2:11][CH2:12][CH2:13]3)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 69073906(6R*,9aS*)-6-(3-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 69071146(6R*,9aS*)-6-(3-fluorophenyl)octahydroquinolizin-4-oneYield 82.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (20 mg) was added to a solution of (6R*,9aS*)-6-(3-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one (460 mg) in methanol (10 mL), and the reaction solution was stirred in a hydrogen stream at room temperature for three hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 383 mg of the title compound. The property values of the compound are as follows.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-7df9af89e6dc4c37b4fcdbc3918c31d6
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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