Process for preparing a 4,4-diphenylbutanoic acid derivative
US4777288A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jun 11, 1987 |
| Grant date | Oct 11, 1988 |
| Priority date | — |
| Expiry date | Jun 11, 2007 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C51/367
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel three-step process for preparing 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid is disclosed, which involves (1) reducing 4-(3,4-dichlorophenyl)-4-ketobutanoic acid to 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid; (2) then converting the intermediate hydroxy acid formed in the first step to 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone, and (3) thereafter reacting the resulting gamma-butyrolactone compound with benzene in a Friedel-Crafts type reaction to form the desired final product. The latter compound is known to be useful as an intermediate leading to cis-(1S)(4S)- -N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine (sertraline), which is known to be a preferred anti-depressant agent in the field of medicinal chemistry. The aforementioned 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid are both novel compounds.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.