The Upjohn Co.

Joel E Huber

Verlan H VanRheenen

Bruce Allen Pearlman

John M Beaton

Amphlett Greg Padilla

Douglas A Livingston

Scott Denmark

Max E Breuer

Jeffrey A Fleming

The present invention involves improved processes for the dehalogenation of 9.alpha.-halosteroids (I) ##STR1## to produce the corresponding 11.beta.-hydroxy steroids (II) ##STR2## which are known to be useful as pharmaceutical, where the improvements comprise (1) adding the 9.alpha.-halo steroid (I) to the chromium and (2) using catalytic amounts of chromium in the presence of a means of converting chromium (II) to chromium (III).

9.alpha.-dehalogenation process

Disclosed is a process for the production of a .DELTA..sup.17(20) -steroid of the formula ##STR1## which comprises starting with a 16-unsaturated corticoid of the formula ##STR2## and contacting the 16-unsaturated corticoid (I) with a methylating agent in the presence of a copper catalyst and a silylating agent.

16.alpha.-methylation process

C.sub.16 -unsaturated corticoids are readily transformed to the corresponding 16.alpha.-methyl-17.alpha.-hydroxy corticoids by use of a .DELTA..sup.17 (.sup.20)-20-silyl ether.

The invention is the compound 17.beta.-cyano-9.alpha., 17.alpha.-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17.alpha.-halo silyl ethers (II).

17.beta.-cyano-9.alpha.,17.alpha.-dihydroxyandrost-4-en-3-one

C.sub.16 -unsaturated corticoids are readily transformed to the corresponding 16.alpha.-methyl-17.alpha.-hydroxy corticoids by use of a .DELTA.17(20)-20-silyl ether.

16.alpha.-methyl-17.alpha. 20-epoxysteroid and process

16.alpha.-methylated.DELTA.17(20)-corticoids

.alpha.-Halomethylbenzodiazepines (II) are produced by direct halogenation of methylbenzodiazepines (I) using sulfuryl halide.

Process to prepare .alpha.-chloroalprazolam

This invention discloses a general process for the production of corticoids from respective steroid-type compounds having a double bond from C-16 to C-17. The invention provides a viable alternative synthesis of 17.alpha.-hydroxy-progesterones and like corticoids.

Process for preparation of 16 .alpha.-methyl corticoids from

A process for preparing 19-norandrostenedione. Also provides key intermediates of 19-norandrostenedione and methods for preparing them in high yields.

Grignard reagents prepared from 5-halopentan-2-one propylene ketals

The present invention discloses a process for the production of androsta-4,9(11)-diene-3,17-dione type compounds from 9.alpha.-hydroxyandrostenedione type compounds by non-aromatic oxygenated strong acid dehydration.

Growing community of inventors

Kalamazoo, MI, United States of America

Joel E Huber