Merck + Co., Inc.

Newton L Abramson

Sandor Karady

Kevin M Anderson

Anthony O King

Richard F Shuman

Alan W Douglas

Leonard M Weinstock

Edward G Corley

Seemon H Pines

Robert F Czaja

Donald F Reinhold

Torleif Utne

A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si-OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.

Trialkylsilyl trifluoromethanesulfonate mediated .alpha.-methylenic

A novel, facile, and specific process for .alpha.-iodinating or .alpha.-brominating the .alpha.-methylenic carbon of a straight chain, branched chain, or cyclic secondary amide, such as a lactam or an azasteroid, comprises reacting the amide with trialkylsilyl-X (R.sub.3 Si--X), where X is Br, I, or Cl, and R is methyl, ethyl, or n-propyl, in the presence of I.sub.2 or Br.sub.2. The .alpha.-iodo- or .alpha.-bromo-amide is useful for making the .alpha.,.beta.-unsaturated amide through dehydrohalogenation.

Process for iodinating or brominating the .alpha.-methylenic carbon of a

A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si--OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.

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

A process for the preparation of (S)- or L-3-(3,4-dihydroxyphenyl)alanine (L-dopa) is described. The process utilizes water as reaction process solvent and proceeds via formation of an intermediate which can be kinetically resolved in a polar solvent to a precursor of the desired isomer and in which the undesired isomer can be efficiently racemized for reuse.

Process for L-dopa

Haloalkyl derivatives of aromatic compounds are prepared via reaction with dialkoxy or aralkoxy alkanes in the presence of a Lewis acid.

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Edison, NJ, United States of America

Newton L Abramson