Schering Corporation

Lydia Peer

Joseph Mayer

Esther Babad

Wei K Chang

Elijah J Gold

There is disclosed a multistep process for producing (-)-5-[(R)-1-hydroxy-2-((R)-1-methyl-3-phenyl-propyl)aminoethyl]salicylami de in high yields which does not require chromatography. The process is stereoselective for the desired products starting with the reaction of D-(+)-alpha-methylbenzylamine with benzylacetone followed by reduction of the resulting Schiff's base to form an amine as an R,R: R,S diastereomeric mixture, resolution of the mixture to obtain the R,R stereoisomer as a salt, conversion to a free base, reaction of the R,R free base with an O-protected alpha-bromo-3-carbamoyl-acetophenone to produce the corresponding R,R-ketobenzamide, reduction to produce a mixture of S,R,R;R,R,R hydroxybenzamide, removal of the protecting groups, resolution of the deprotected product and then conversion to the free R,R-amine.

Preparation of

A compound of the formula ##STR1## wherein X and Y are independently selected from hydrogen, halogen, trifluoromethyl, nitro, C.sub.1 to C.sub.6 alkyl and C.sub.1 to C.sub.6 alkoxy, and Z is C.sub.1 to C.sub.6 alkyl or hydrogen is disclosed.

Benzodiazepine intermediates

This invention describes a novel process whereby meta-substituted anilides are nitrated in the para position in high yields.

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West Orange, NJ, United States of America

Lydia Peer