2-amino-1-phenylpropanols, stereospecific synthesis thereof, and method of optically resolving the same
US5962737A · kind A · utility
Inventor
Key dates
| Filing date | Jan 8, 1997 |
| Grant date | Oct 5, 1999 |
| Priority date | — |
| Expiry date | Jan 8, 2017 |
Classification
- Technology area (CPC A)Human Necessities
- CPC primaryA61K9/143
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
Stereospecific synthesis of the racemic threo isomers of 2-nitro-1-phenylpropanols by reacting a benzaldehyde derivative with nitroalkane in the presence of a tertiary amine and reducing 2-nitro-1-phenylpropanols with, for example, lithium aluminum hydride to 2-amino-1-phenylpropanols is described. Also described are phase transfer resolution of racemic mixtures of 2-amino-1-phenylpropanol and its derivatives into their optically pure isomers by reacting a racemic mixture with the mono alkali metal salt of a tartaric acid ester in a two phase system of a hydrocarbon and water. The specification further describes therapeutically useful optically pure isomers of threo-2-amino-1-(dialkoxy or alkoxy) phenylpropanols and acid addition salts thereof.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.