Process for trans-6-[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-one inhibitors of cholesterol synthesis
US5149837A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Feb 12, 1992 |
| Grant date | Sep 22, 1992 |
| Priority date | — |
| Expiry date | Feb 12, 2012 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D405/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
An improved process for the preparation of trans-6-[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where 1,6-heptadien-4-ol is converted in eight operations to the desired products, as well as an improved process for the preparation of (2R-trans) and trans-(.+-.)-5-(4-fluoro-phenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetr ahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide by a novel synthesis where 4-methyl-3-oxo-N-phenylpentanamide is converted in eight operations to the desired product or alternatively 4-fluoro-.alpha.-[2-methyl-1-oxopropyl]-.gamma.-oxo-N,.beta.-diphenylbenze nebutaneamide is converted in one step to the desired product, and additionally, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide from (R)-4-cyano-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]butanoic acid, as well as other valuable intermediates used in the processes.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.