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

HRID 553879
Notes
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Reaction equation

HRID 553879 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:18][CH2:17][CH2:16][C@@H:15]3[N:10]2[C:11](=[O:19])[CH2:12][CH:13]=[CH:14]3)=[CH:5][CH:4]=1.[H][H]>CO.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:18][CH2:17][CH2:16][C@@H:15]3[N:10]2[C:11](=[O:19])[CH2:12][CH2:13][CH2:14]3)=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 69072392(6R*,9aS*)-6-(4-methoxyphenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 69070867(6R*,9aS*)-6-(4-methoxyphenyl)octahydroquinolizin-4-oneYield 81.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (2 mg) was added to a solution of (6R*,9aS*)-6-(4-methoxyphenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one (28 mg) in methanol (5 mL), and the reaction solution was stirred in a hydrogen stream at room temperature for 13 hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 23 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-962f1dadef664bf0a55ec32702bb57ad
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08048878B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes