Merck + Co., Inc.

Ann E DeCamp

Ralph P Volante

Nobuyoshi Yasuda

Ichiro Shinkai

Edward J Grabowski

Thomas R Verhoeven

Mark A Huffman

Anthony O King

Lyndon C Xavier

Alan T Kawaguchi

Sander G Mills

Leonard M Weinstock

David J Mathre

Guo-Jie Ho

Robert K Anderson

A process is described for the removal of a silyl protecting group from the 4-hydroxy group of a tetrahydro-pyran-2-one moiety.

Process for the desilylation of a 4-silyloxy-tetrahydro-pyran-2-one

The present invention is directed to a compound represented by the structural formula: ##STR1## wherein Z-- represents a negatively charged counterion.

Boronic acid compound

A chiral resolution process is described for the purification of a substituted chiral quinazoline, by salt formation with a resolving agent, followed by crystallization.

Chiral resolution process

The present invention is directed to a process of making 2-aryl carbapenems of formula 1 from a compound of formula A. ##STR1## wherein compound A is reacted with a silyl protected boronic acid compound of the formula B: ##STR2## and wherein Ar is selected from the group consisting of: ##STR3##

Preparation of 2-aryl carbapenems

An asymmetric synthesis of (S)-(-)-6-chloro-4-cyclopropyl-3,4-dihydro-4-[(2-pyridyl)ethynyl]-2(1H)-qu inazolinone comprises the chiral addition of 2-pyridylacetylide to N.sup.1 -protected 6-chloro-4-cyclopropyl-2-quinazolinone followed by removal of the protecting group.

Asymmetric synthesis of (S)-(-)-6-chloro-4-

A unique process for preparing certain (2R-trans)hexahydroaroquinolizines, especially (2R-trans)-N-[2-(1,3,4,6,7,12b-hexahydro-2'-oxospiro[aro-[2,3-a]-quinolizi ne-2,4'-imidazolidin]-3'-yl) ethyl)-methanesulfonamide from (2R-trans)-N-[2-[(2-cyano-(1,3,4,6,7,12b-hexahydro-aro-[2,3-a]quinolizin-2 -yl)amino]ethyl]methanesulfonamide is described.

Process for certain (2R-trans)hexahydroaroquinolizines

This invention discloses novel intermediates and novel process for their preparation where said intermediates are useful for the preparation of 5-oxygenated derivatives (T) of lovastatin and analogs thereof at the 8-acyl side chain and 6-position of the polyhydronaphthyl ring. Said derivatives of lovastatin (T) and analogs thereof are useful in treating hypercholesterolemia and are disclosed in the U.S. Pat. No. 4,963,538. ##STR1##

Processes and intermediates for the preparation of 5-oxygenated HMG-CoA

A unique process for preparing certain (2R-trans)hexahydroaroquinolizines, especially (2R-trans)-N-[2-(1,3,4,6,7,12b-hexahydro-2'-oxospiro[aro-[2,3-a]-quinolizi ne-2,4'-imidazolidin]-3'-yl)ethyl)-methanesulfonamide from (2R-trans)-N-[2-[(2-cyano-(1,3,4,6,7,12b-hexahydro-aro-[2,3-a]quinolizin-2 -yl)amino]ethyl]methanesulfonamide is described.

A novel hydrogenation process, using a homogenous iridium or rhodium catalyst for the reduction of both double bonds of des-(.alpha.-methylbutyryl)-C-8-hydroxy lovastatin and C-8-amino, C-8-alkoxy and C-6-substituted analogs, is disclosed.

Hydrogenation process for the formation of tetrahydro HMG-CoA reductase

A novel acylation process using an alkali metal bromide and a dialkylaminopyridine to form a sterically hindered ester functionality from an alkanoyl chloride and an alcohol is disclosed.

Acylation process for the synthesis of HMG-CoA reductase inhibitors

A novel hydrogenation process, using a homogenous iridium or rhodium catalyst for selectively adding hydrogen to the 3,5 positions in the polyhydronaphthyl ring of lovastatin, simvastatin or C-8-acyl or C-6-substituted analogs thereof, is disclosed.

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North Plainfield, NJ, United States of America

Ann E DeCamp