Schering Corporation

Schering-Plough Corporation

Esther Babad

Martin Steinman

Nicholas I Carruthers

Lydia Peer

Elijah H Gold

Wei K Chang

Joseph Mayer

Elijah J Gold

There is disclosed an improved process for preparing albuterol which comprises reacting a 5-(haloacetyl)-2-hydroxybenzaldehyde with 1,1-dimethylethanamine in an organic solvent and in an inert atmosphere to form 5-[[(1,1-dimethylethyl)amino]acetyl]- 2-hydroxybenzaldehyde and reducing the carbonyl functions to the corresponding hydroxy groups to form albuterol.

Method for the preparation of .alpha..sup.1

There is disclosed an improved process for preparing albuterol which comprises reacting a 5-(haloacetyl)-2-hydroxybenzaldehyde with 1,1-dimethylethanamine in an organic solvent and in an inert atmosphere to form 5-[[(1,1-dimethylethyl)amino]acetyl]-2-hydroxybenzaldehyde and reducing the carbonyl functions to the corresponding hydroxy groups to form albuterol.

Intermediates in the preparation of alpha1(((1,1-dimethylethyl) amino)

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

A process is provided for the preparation of amines via the desulfonylation of sulfonamides by means of sodium bis-(2-methoxyethoxy) aluminum hydride.

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West Orange, NJ, United States of America

Esther Babad