4a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline → 4a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

HRID 26477Notes

Reaction equation

HRID 26477 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:18][CH2:17][CH2:16][CH:15]=[C:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 132819714a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 867364784a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline (6.0 g) in 250 ml of glacial acetic acid was treated with 1 g of 5% palladium on carbon and the mixture hydrogenated under 40 psi of hydrogen for 24 hours in a Parr shaker. The catalyst was then filtered off and the filtrate evaporated. The residual 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline was recrystallized from ethanol, m.p. 189-190.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate evaporated
  3. customThe residual 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline was recrystallized from ethanol

Sources & evidence

ORD record
ord-25e3da5125654589bbcf986fa5a9b343
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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