(6S,9aR)-6-(4-chlorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one → (6S,9aR)-6-(4-chlorophenyl)octahydroquinolizin-4-one

HRID 16366Notes

Reaction equation

HRID 16366 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1>[Pt]=O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

4

Reactant 1

HCID 67462933(6S,9aR)-6-(4-chlorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one

Product 1

HCID 67462899(6S,9aR)-6-(4-chlorophenyl)octahydroquinolizin-4-oneYield 79.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (95 mg) was added to a methanol solution (50 mL) of (6S,9aR)-6-(4-chlorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one (1.09 g). The resulting reaction solution was stirred under hydrogen atmosphere at room temperature for 1 hr and filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) to give 877 mg of the title compound. The physical property values of this compound were as follows:

Workup

  1. customThe resulting reaction solution
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-c0b01ea6dbaf46ad9beb9f4fc0269988
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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