Acetic Acid → 8-(Methoxycarbonylethyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one

HRID 1831751Notes

Reaction equation

HRID 1831751 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[CH:16]=[CH:15][C:14]2[NH:13][C:12](=[O:17])[CH:11]3[CH2:18][CH2:19][CH2:20][CH:10]3[C:9]=2[CH:8]=1)=[O:4].C(O)(=O)C.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[NH:13][C:12](=[O:17])[CH:11]3[CH2:18][CH2:19][CH2:20][CH:10]3[C:9]=2[CH:8]=1)=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 69652699HCID 69652699, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 541722578-(Methoxycarbonylethyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.73 g (10.1 mmol) of 8-(methoxycarbonylethenyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one is dissolved in 100 ml of ethyl acetate, and after 273 mg of 10% Pd-C and 0.1 ml of acetic acid are added, it is stirred for 24 hours in a hydrogen atmosphere. After filtration, the filtrate is concentrated by evaporation and purified by column chromatography on silica gel with hexane-ethyl acetate: 2.7 g.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. custompurified by column chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-bfc880d7c700424386dfc078e5fae143
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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