Merck + Co., Inc.

Edward G Corley

Andrew S Thompson

Ralph P Volante

Robert D Larsen

Kai Rossen

Edward J Grabowski

Ian W Davies

Philip J Pye

Nobuyoshi Yasuda

Meyer Sletzinger

Thomas R Verhoeven

Thomas M Liu

James M McNamara

Ichiro Shinkai

Leonard M Weinstock

Paul J Reider

Raman Kumar Bakshi

Sandor Karady

David J Mathre

Ross A Miller

Daniel Richard Sidler

Jerry Anthony Murry

Newton L Abramson

Jess Sager

Karen M Conrad

Jean-Francois Marcoux

Louis Matty

Ashok Maliakal

Genevieve N Boice

Cecile G Savarin

James D Carroll

Martha Huntington

A novel process is provided for the preparation of 4-aryl piperidines, and the useful intermediates obtained therein. These compounds are intermediates for the synthesis of melanocortin-4 receptor (MC-4R), which are useful for the treatment of disorders such as obesity, diabetes, male sexual dysfunction, and female sexual dysfunction.

Process and intermediates for the preparation of 4-aryl piperidines

The instant invention involves a process for oxidizing compounds containing an allylic group, i.e. those containing an allylic hydrogen or allylic alcohol group, to the corresponding enones, using a ruthenium-based catalyst in the presence of a hydroperoxide. Particularly, &Dgr;-5-steroidal alkenes can be oxidized to the corresponding &Dgr;-5-7-keto alkenes.

Process for oxidation of steroidal compounds having allylic groups

The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.

Intermediates useful in a process for synthesizing COX-2 inhibitors

The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1##

Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2

Process for synthesizing COX-2 inhibitors

An improved synthesis of a highly potent HIV reverse transcription inhibitor is disclosed, involving an acetylide and a trifluoromethyl ketone which produces a chiral product in the presence of a chiral amino alcohol.

Asymmetric synthesis of

An improved synthesis of cyclopropylacetylene involving cyclization of 5-halo-1-pentyne in strong base is disclosed, and is useful for preparing compounds with a cyclopropylethynyl substituent, such as an intermediate for a highly potent HIV reverse transcriptase inhibitor or other pharmaceutically active compounds.

Synthesis of cyclopropylacetylene

Oxazaborolidine-borane complexes are prepared by adding a C.sub.5-8 alkane, typically hexane, to an aged solution of oxazaborolidine and a source of borane such as borane-dimethyl sulfide or gaseous diborane to crystallize the oxazaborolidine complex.

Preparation of oxazaborolidine borane complex

A process is described for the preparation of an optically active carboxylic acid or ester derivative thereof from a ketene and an optically active .alpha.-hydroxyester or an .alpha.-hydroxy amide.

Resolution of a carboxylic acid

This invention relates to a process for preparing .beta.-lactams by electrochemically deblocking N-substituting .beta.-lactams using anodic oxidation.

Process for deblocking N-substituted .beta.-lactams

An enantioselective synthesis of 1,3,4,6,7,12b(S)-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin-2-one provides a key intermediate for the preparation of the .alpha..sub.2 -adrenergic antagonist (2R,12bS)-N-(1,3,4,6,7,12-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin-2-yl) -N-methyl-2-hydroxyethanesulfonamide hydrochloride, useful as an anti-depressant.

Enantioselective synthesis of

This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-cyano-3(R)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.

Process for the preparation of HMG-CoA reductase inhibitors and

This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-halo-3(S)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.

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Old Bridge, NJ, United States of America

Edward G Corley