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

HRID 553895Notes

Reaction equation

HRID 553895 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:20][CH2:19][CH2:18][C@@H:17]3[N:12]2[C:13](=[O:21])[CH2:14][CH:15]=[CH:16]3)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[H][H]>CO.[Pt]=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:20][CH2:19][CH2:18][C@@H:17]3[N:12]2[C:13](=[O:21])[CH2:14][CH2:15][CH2:16]3)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 69074738(6R*,9aS*)-6-(4-carbomethoxyphenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 69070572(6R*,9aS*)-6-(4-carbomethoxyphenyl)octahydroquinolizin-4-oneYield 85.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (10 mg) was added to a solution of (6R*,9aS*)-6-(4-carbomethoxyphenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one (145 mg) in methanol (5 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 to obtain 125 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

Sources & evidence

ORD record
ord-87e68976cca54d9b972d7e7996ecab57
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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