Process for preparing &bgr;-hydroxycarbamates and their conversion to oxazolidinones
US6372911B1 · kind B1 · utility
Assignee
Inventors
Key dates
| Filing date | Jan 13, 2000 |
| Grant date | Apr 16, 2002 |
| Priority date | — |
| Expiry date | Jan 13, 2020 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D263/38
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for preparing a &bgr;-hydroxy carbamate product is disclosed. The process comprises reacting an olefin compound containing at least one carbon-carbon double bond with a carbamate in an aqueous solvent and in the presence of a base, an osmium catalyst, a co-oxidant selected from a halohydantoin, a haloisocyanuric acid, and an alkali metal salt of a haloisocyanuric acid, and optionally an asymmetric ligand, to form a reaction mixture containing the &bgr;-hydroxy carbamate product. The process optionally further comprises treating the &bgr;-hydroxy carbamate product with additional base to form an oxazolidinone. The oxazolidinones are useful as chiral auxiliary agents and as intermediates for the formation of pharmaceutically active substances such as alpha 1 a adrenergic receptor antagonists. A process for preparing nitrogen-functionalized derivatives of the oxazolidinones is also disclosed.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.