HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic aicd
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | Ethyl 5-[[1-[1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoate | HCID 22339324 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic aicd | HCID 22339261 | 35% |
Reaction Steps
Ethyl 5-[[1-[1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoate (100 mg, 0.17 mmol) prepared in Example 94 was dissolved in THF (3 ml), ethanol (2 ml) and water (2 ml), to which lithium hydroxide monohydrate (21 mg, 0.51 mmol) was then added and stirred at room temperature for 3 hours. The reaction mixture was neutralized with 1N hydrochloric acid and then extracted with ethyl acetate. After the organic layer was dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=4/1) to give the titled compound (33 mg, yield: 35%) as a colorless oil. (cis:trans=1:1.5)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06930104B2 |
| Source dataset | uspto-grants-2005_08 |
| ORD ID | ord-0cb759a2f55543b9a4643d503acee821 |
| Source note | uspto-grants-2005_08 |