L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo2.2.1!heptane compound and the preparation of 2-azabicyclo2.2.1!heptane compounds
US5684159A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 16, 1996 |
| Grant date | Nov 4, 1997 |
| Priority date | — |
| Expiry date | Oct 16, 2016 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A method according to the invention is directed to the preparation of a 2-azadihydroxybicyclo2.2.1!heptane compound of formula ##STR1## wherein * represents an R chirality, *' represents an S chirality, R is hydrogen or, respectively, a group of formula ##STR2## wherein R.sub.1 is alkyl and Ar is optionally substituted aryl, comprising bishydroxylating a bicyclo2.2.1!heptene compound of formula ##STR3## wherein *, *' and R are as previously defined, in the presence of about 0.1 mol to about 5 mol % of a metal osmate compound or about 0.06 mol % to about 0.07 mol % osmium tetroxide, and an oxidizing agent capable of regenerating osmium tetroxide. The invention is also directed to the treatment of the (1R) diastereomer of the 2-azadihydroxybicyclo2.2.1!heptane compound (I) wherein R is a group of formula II with L-tartaric acid, and the L-tartaric acid salt product thereof. Furthermore, the invention is directed to using the (1R) diastereomer of the 2-azadihydroxybicyclo2.2.1!heptane compound in an acid facilitated acetalizing or ketalizing reaction that results in the protection of the dihydroxy moieties thereof in isopropanol. In addition, the invention is directed to oxidizing a b…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.