Merck + Co., Inc.

Alan W Douglas

Kevin M Anderson

Thomas R Verhoeven

Edward J Grabowski

Ulf H Dolling

Sandor Karady

Anthony O King

Richard F Shuman

Newton L Abramson

Apurba Bhattacharya

Lisa DiMichele

Steven A King

Andrew S Thompson

Ralph P Volante

Nobuyoshi Yasuda

Ioannis N Houpis

Audrey Molina

Joseph D Armstrong, Iii

Jennifer L Keller

.beta.- or .gamma.-Ketoesters and .beta.- or .gamma.-ketoamides are asymmetrically reduced with a Ru(II)-BINAP derived catalyst at about 40.degree. C. and about 50 N/mm.sup.2 of hydrogen in the presence of a strong acid.

Ruthenium-phosphine complex catalysts for asymmetric hydrogenations

.beta.- or .gamma.-Ketoesters and .beta.- or .gamma.-ketoamides are asymmetrically reduced with a Ru(II)-BINAP derived catalyst at about 40.degree. C. and about 50N/mm.sup.2 of hydrogen in the presence of a strong acid.

Asymmetric hydrogenation of beta- or gamma-ketoesters and beta- or

4-Chloro-2-cyclopropylcarbonylaniline is prepared by condensation of 4-chloroaniline with 4-chlorobutyronitrile to form a 2-(4-chlorobutyryl)-4-chloroaniline, followed by ring closure of the 4-chlorobutyryl group to a cyclopropylcarbonyl moiety.

Process for the preparation of 4-chloro-2-cyclopropylcarbonylaniline

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 process for dehydrogenating a compound of the formula ##STR1## which comprises reacting the compound with a silylating agent in the presence of a quinone to introduce a .DELTA..sup.1 double bond.

Dehydrogenation process intermediates

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.

Dehydrogenation process

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Monmouth Junction, NJ, United States of America

Alan W Douglas