L-tartaric acid salt of a (1R) diastereomer of a

Details L-tartaric acid salt of a (1R) diastereomer of a L-tartaric acid salt of a (1R) diastereomer of a

1996-10-16

1997-11-04

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20952

Patent

active

056841590

ABSTRACT:
A method according to the invention is directed to the preparation of a ##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 ##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 of formula II with L-tartaric acid, and the L-tartaric acid salt product thereof. Furthermore, the invention is directed to using the (1R) 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 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%.

REFERENCES:
Katagiri Muto Nomura Higashikawa Kaneko Synthesis of Carbocyclic BorohydrideMediated Carbon-Nitrogen Bond Chemical and Pharm. Bull., vol. 39, No. 5, 1991 (pgs. 1112-1122).
Katagiri Muto Kaneko Stereospecific synthesis of Carbocyclic Nucleosides Tetrahedron Letters, vol. 30, No. 13, 1989, pp. 1645-1648.

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