The Dow Chemical Company

Merrell Dow Pharmaceuticals

Hoechst Marion Roussel

University of California

Merrell Pharmaceuticals, Inc.

Other

Purdue Research Foundation

Micromidas, Inc.

Aventis Pharmaceuticals Inc.

Aventisub Ii Inc.

Christian T Goralski

George A Burk

Craig E Mixan

R Garth Pews

Bakthan Singaram

Jonathan C Evans

Thomas C Klingler

Cynthia L Rand

Paul C Vosejpka

Herbert C Brown

Daniel Randolph Henton

David H Louks

Lawrence W Nicholson

Sandra K Stolz-Dunn

Mark R Smit

Gary B Fisher

Mark A Nitz

Sandra Stolz-Dunn

Makoto Nathanael Masuno

Ryan L Smith

Alex Benjamin Wood

Charles E Reineke

Dimitri A Hirsch-Weil

Curtis D Pfeiffer

Robert Joseph Araiza

Brian D Scherzer

James E Hitt

John F Hoops

Timothy G Fawcett

David W Ziettlow

Yolanda M Puga

William Chrisman

Paul A Wolf

Kuttanchery Ananthanarayanan Ramanarayanan

John Harrison

Joseph C Fuller

Kuttanchery A Ramanarayanan

Provided herein are methods of producing halomethylfuroic and acyloxymethylfuroic acid and ester compounds from furfural starting compounds. For example, 5-chloromethyl-2-furoic acid may be produced from 5-chloromethylfurfural, in the presence of various oxidants. Salts of the furoic acids may also be produced.

Oxidation chemistry on furan aldehydes

Chiral amino alcohols and process for preparation of same

The present invention is directed to a method for producing vinyl GABA by submitting 5-vinylpyrrolidin-2-one to a basic hydrolysis.

Process for the production of vinyl-GABA

The present invention relates to a process for preparing a compound of formula (I): ##STR1## wherein R is C.sub.1 -C.sub.10 alkyl, phenyl or substituted phenyl, comprising treating a compound of formula (II): ##STR2## with bis(tributyltin) oxide in an organic solvent selected from the group consisting of o-xylene, m-xylene, p-xylene and mixed xylenes; and subsequently treating the reaction mixture with a compound of formula (III): ##STR3## wherein X is halogen and R is defined as above.

Process for preparing 6-0-monoesters of castanospermine

Process for the preparation of

The present invention relates to a novel process for preparing (E)-1-amino-2-(fluoromethylene)-4-(p-fluorophenyl)butane, also known in the art as (E)-(p-fluorophenethyl)-3-fluoroallylamine, novel intermediates thereof, a novel process for the preparing (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol, and a novel process for preparing alkali metal salts of diformylamide.

Process for the separation of enantiomers

The present invention relates to a novel process for preparing alkali metal salts of diformylamide and a novel crystalline form of sodium diformylamide.

Process for the preparation of alkali metal salts of diformylamide

The present invention relates to novel, powerful reducing agents, lithium aminoborohydrides which are prepared by addition of BH.sub.3 .cndot.THF to the corresponding dialkylamine at 25.degree. C. to give the intermediate amineborane complex. Subsequent deprotonation by strong base, e.g. n-BuLi, yields the aminoborohydride quantitatively. Lithium aminoborohydrides are powerful reducing agents, comparable in strength to lithium aluminum hydride. The activity is determined by the dialkylamine. Lithium pyrrolidinoborohydride has unique activity and selectivity in its reducing properties. Esters, lactones and anhydrides are reduced cleanly at 25.degree. C. to give the corresponding alcohols, while carboxylic acids are not reduced. Test reductions show that lithium pyrrolidinoborohydride is also capable of reducing a wide range of functional groups including amides, epoxides, oximes, nitriles and halides.

Synthesis of lithium aminoborohydrides and reactions thereof

The present invention relates to a process for the synthesis of chiral enantiomerically pure .beta.-amino alcohols which are extraordinarily important as therapeutic agents for the treatment of a variety of human disorders and as chiral auxiliaries in organic synthesis. The hydroboration of enamines is a versatile and convenient method for the synthesis of both racemic and enantiomerically pure .beta.-amino alcohols in high yields. This methodology enables the synthesis of virtually any .beta.-amino alcohol. Hydroboration of these enamines with chiral organic borohydrides, e.g. either mono- or diisopinocampheylborane, followed by oxidation with aqueous or solid NaOH/30% H.sub.2 O.sub.2 or Me.sub.3 NO, gives the corresponding chiral .beta.-amino alcohol. Enantiomeric excesses ranged from 60% for reactions run at 25.degree. C. to greater than 99% for reactions run at -25.degree. C.

Asymmetric synthesis of .beta.-amino alcohols from chiral or achiral

The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

Organoboron reagents for the preparation of unsubstituted propargylic

The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields. Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

New organoboron reagents for the preparation unsubstituted propargylic

Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.

Synthesis of alkenes from enamines via hydroboration

A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.

Stereospecific synthesis of [E]-alkenes from enamines via hydroboration

Growing community of inventors

Midland, MI, United States of America

Christian T Goralski