L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo›2.2.1!heptane compound and the preparation of 2-azabicyclo›2.2.1!heptane compounds

Abstract

A method according to the invention is directed to the preparation of a 2-azadihydroxybicyclo›2.2.1!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 bicyclo›2.2.1!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-azadihydroxybicyclo›2.2.1!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-azadihydroxybicyclo›2.2.1!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 bis O-protected derivative of the (1R) diastereomer of the 2-azadihydroxybicyclo›2.2.1!heptane compound to a corresponding lactam compound in the presence of about 0.01 mol % to about 1 mol % of RuO.sub.2 with about 3 equivalents of an oxidant to form the lactam compound with in an enantiomeric excess ("ee") of greater than or equal to about 95%.

Dependencies are inferred from the claim text.