Process for preparing 3-hydroxymethyl-4-(aryl or heterocyclic)-cyclopentanones
US6506908B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Apr 20, 2001 |
| Grant date | Jan 14, 2003 |
| Priority date | — |
| Expiry date | Apr 20, 2021 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2602/18
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Processes are disclosed for preparing 3-hydroxymethylcyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists. A process is described in which the compounds are prepared by opening the cyclopropyl ring of a (1-alkoxycarbonyl-2-oxo)-trans-bicyclo[3.1.0]hexane compound by addition of a nucleophile to the cyclopropyl ring, and then decarboxylating the resulting 2-alkoxycarbonyl-3-(Nu-methyl)-cyclopentanone (Nu=the added nucleophilic group) via base solvolysis. Also described is a process for preparing the bicyclo[3.1.0]hexane precursors by the catalyzed cyclopropanation of a suitable alpha-diazo-beta-ketoester. The preparation of the alpha-diazo-beta-ketoesters and precursors thereto are also disclosed.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.