Stereopreferential synthesis of 3-(1-phenylprop-2-yl)-5-phenyloxazolidinones
US5468865A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | May 3, 1994 |
| Grant date | Nov 21, 1995 |
| Priority date | — |
| Expiry date | May 3, 2014 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The (R,R)-diastereoisomer of oxazolidin-2-ones, which are chemical intermediates for the preparation therapeutic agents useful in the treatment of diabetes and hyperglycemia, are prepared substantially free of isomeric forms through reduction of an acid addition salt of an (R)-N-protected-N-phenylcarboxymethyl-1-phenylprop-2-ylamine to form a secondary alcohol of predominantly the (R,R) chiral form in preference to others, removal of the protecting group to form a secondary amine, and allowing the secondary amine to react with a source of carbonyl groups. A typical embodiment involves the preparation of (R,R)-3-[1-(3,4-dimethoxyphenyl)prop-2-yl]-5-(3-chlorophenyl)oxazolidin-2- one in which both the chemical purity and optical purity are in excess of 99%.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.