Synthesis of 1,3-oxathiolane sulfoxide compounds
US5654441A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Sep 14, 1995 |
| Grant date | Aug 5, 1997 |
| Priority date | — |
| Expiry date | Sep 14, 2015 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D327/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process for the production of a 1,3-oxathiolane sulfoxide of the formula ##STR1## wherein X is an amino group of the formula --NHR, wherein R is hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, nitrophenyl, (C.sub.1 -C.sub.4 alkoxy)phenyl, furfuryl, halophenyl, tolyl, napthyl, biphenyl or hydroxyphenyl; or X is an alkoxy group of the formula --OR.sup.1 wherein R is C.sub.1 -C.sub.6 alkyl, which process comprises oxidizing a 1,3-oxathiolane of the formula ##STR2## wherein X is as defined above, in the presence of an effective amount of aqueous hydrogen peroxide and a sterically-hindered organoselenium compound of the formula ##STR3## wherein R.sup.2 is aryl, mono-, di- or tri-substituted with C.sub.1 -C.sub.3 alkyl, to the produce the 1,3-oxathiolane sulfoxide. This process stereoselectively produces the cis stereoisomer of the 1,3-oxathiolane sulfoxide. Additionally, there is disclosed a novel method for the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin compounds using this process.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.