(6R*,9aS*)-6-(2-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one → (6R*,9aS*)-6-(2-fluorophenyl)octahydroquinolizin-4-one

HRID 553911Notes

Reaction equation

HRID 553911 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[N:9]1[C:10](=[O:18])[CH2:11][CH:12]=[CH:13]2.[H][H]>CO.[Pt]=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[N:9]1[C:10](=[O:18])[CH2:11][CH2:12][CH2:13]2

Participants

5

Reactant 2

HCID 69074505(6R*,9aS*)-6-(2-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 69077331(6R*,9aS*)-6-(2-fluorophenyl)octahydroquinolizin-4-oneYield 83.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (16 mg) was added to a solution of (6R*,9aS*)-6-(2-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one (368 mg) in methanol (8 mL), and the reaction solution was stirred in a hydrogen stream at room temperature for two 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 309 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-b04c4557342a4f12afc992cdb552b245
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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