G.d. Searle & Company

Monsanto Company

Entegris, Inc.

Louisiana State University and Agricultural & Mechanical College

Scott A Laneman

Daniel L Flynn

Roger A Nosal

Norman A Abood

Lori A Schretzman

Richard A Mueller

Daniel P Getman

Gary A DeCrescenzo

Michael L Vazquez

Robert M Heintz

John S Ng

Deborah E Bertenshaw

Chin Liu

Albert S Chan

Claire A Przybyla

John J Freskos

Suhong Zhang

George G Stanley

Amihia Eisenstadt

David J Ager

Vagulejan Balasanthiran

Thomas H Baum

Thomas M Cameron

David Kuiper

David M Ermert

Jonathan W Dube

Paul Hinkle

Victoria Weidner

James M Stubbs

Thomas Kermis

Jon Alkema

Johathan W Dube

Provided are complexes useful in the conversion of chloro- and bromo-silanes to highly desired iodosilanes such as HSiIand HSiI, via a halide exchange reaction. The species which mediates this reaction is an iodide reactant comprising aluminum.

Method of preparing iodosilanes and compositions therefrom

Provided is methodology for the preparation of highly-desired iodosilanes such as HSiIand HSi, via a reaction of alkylaminosilanes with certain substituted acid iodides. In one embodiment, bis(diethylamino)silane is reacted with benzoyl iodide to provide diiodosilane.

Method for preparing iodosilanes

The disclosure provides methodology for the synthesis of mono-alkylated cyclopentadiene structures, which can be obtained via fulvene intermediates. In one embodiment, the cyclopentadiene ring is substituted with a trialkylsilyl moiety, which enables the further reaction with certain metal halides to form metal adducts. For example, the monoalkyl cyclopentadienes substituted with a trimethylsilyl group can be reacted with TiClto provide R*CpTiClcomplexes, wherein R* is a group of the formula wherein Rand Rare as defined herein.

Monoalkyl cyclopentadiene compounds and processes for preparing same

The disclosure provides a process for preparing bis(monoalkyl-substituted cyclopentadiene) tungsten hydride compounds, for example bis(isopropylcyclopentadienyl)tungsten dihydride, via the corresponding magnesium compound and tungsten hexachloride, followed by treatment with a hydride reagent. Also provided is a process for preparing bis(monoalkyl-substituted cyclopentadiene) metal halide compounds. This latter aspect is achieved by reaction of the corresponding magnesium compound with a metal halide. Exemplary metals in this process include hafnium, zirconium, titanium, tantalum, niobium, tungsten, and molybdenum.

Organometallic compounds and processes for preparing same

Provided is a process for the mono-alkylation of cyclopentadiene, utilizing a cyclopentadiene magnesium halide and a metal salt of an alkyl or aryl sulfonate as co-reactant with an alkyl halide alkylating reactant. The process provides facile methodology for the mono-alkylation of cyclopentadiene, with conversions as high as about 96 percent and selectivity for mono-alkylation (over higher level alkylation, such as di- or tri-) as high as about 99%.

Selective alkylation of cyclopentadiene

The invention is an improved method for the preparation of tertiary phosphines by way of cross-coupling of aryl, alkenyl, cycloalkenyl or aralkyl halides or aryl, alkenyl, cycloalkenyl or aralkyl sulfonate esters with chlorophosphines in the presence of a catalyst and a reductant. The general reaction scheme is shown below: ##STR1## wherein R.sup.1 is aryl, alkenyl, cycloalkenyl or aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl, or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; R.sup.2 and R.sup.3 are independently aryl, alkyl, aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; and n is 2 where R.sup.1 is a difunctional moiety and 1 for any other R.sup.1 ; and X is Cl, Br, I, or OSO.sub.2 Y; wherein Y is alkyl, trihalomethyl, phenyl, halophenyl, or alkylphenyl.

Method for preparation of tertiary phosphines via nickel-catalyzed cross

The invention is an improved method for the preparation of tertiary phosphines by way of cross-coupling of aryl, alkenyl, cycloalkenyl or aralkyl halides or aryl, alkenyl, cycloalkenyl or aralkyl sulfonate esters with chlorophosphines in the presence of a catalyst and a reductant. The general reaction scheme is shown below: ##STR1## wherein R.sup.1 is aryl, alkenyl, cycloalkenyl or aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl, or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; R.sup.2 and R.sup.3 are independently aryl, alkyl, aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl or CoNR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; and n is 2 where R.sup.1 is a difunctional moiety and 1 for any other R.sup.1 ; and X is Cl, Br, I, or OSO.sub.2 Y; wherein Y is alkyl, trihalomethyl, phenyl, halophenyl, or alkylphenyl.

A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide or cyanohydrin from a chiral alpha amino aldehyde.

Method of preparing intermediates for retroviral protease inhibitors

The invention herein is directed to a process for producing a lactam of the formula ##STR1## from a methionine analog of the formula ##STR2## by treating the methionine analog with trimethylsulfonium halide or trimethylsulfoxonium halide in the presence of a base in a suitable aprotic solvent. The invention herein is further directed to the preparation of amidinophenyl pyrrolidinyl .beta.-alanine urea analogs using such methionine and lactam compounds as intermediates, which .beta.-alanine urea analogs are useful as antithrombotics.

Intermediates for amidino phenyl pyrrolidine .beta.-alanine urea analogs

Method for making intermediates useful in the synthesis of retroviral

Process for the preparation of amidino phenyl pyrrolidine beta-alanine

Process for the preparation of amidino phenyl pyrrolidine .beta.-alanine

Novel homogeneous bimetallic hydroformylation catalysts, and processes utilizing these catalysts to convert alkenes, particularly alpha olefins, under mild conditions to a product rich in aldehydes, particularly a product containing a high ratio of linear:branched chain aldehydes. The catalysts can be produced from a binucleating tetratertiaryphosphine ligand capable of strongly coordinating two metal centers and holding them in general proximity to one another. Bimetallic catalyst precursors are produced which, on reaction with carbon monoxide and hydrogen, form the active bimetallic hydroformylation catalyst system.

Homogeneous bimetallic hydroformylation catalysts, and processes

Growing community of inventors

Vernon Hills, IL, United States of America

Scott A Laneman