C - Chemistry – Metallurgy – 07 – J
Patent
C - Chemistry, Metallurgy
07
J
C07J 1/00 (2006.01) C07J 5/00 (2006.01) C07J 7/00 (2006.01) C07J 13/00 (2006.01) C07J 21/00 (2006.01) C07J 31/00 (2006.01) C07J 41/00 (2006.01) C07J 43/00 (2006.01) C07J 51/00 (2006.01)
Patent
CA 2128860
2128860 9315103 PCTABS00024 Novel steroids having a 9.alpha.-hydroxy or a 9.alpha.-carbonate substituent can be prepared from 9.alpha.-hydroxyandrostenedione and can be utilized in the synthesis of commercially valuable corticosteroids such as betamethasone. The 9.alpha.-carbonates are prepared by reaction of the corresponding 9.alpha.-hydroxy steroid with a sequence of excess base, trialkylsilyl chloride, alkyl haloformate and alkanol or by using excess base, alkyl haloformate and alkoxide. 9.alpha.-Carbonate-17-keto compounds can be treated with lithium acetylide and a lithium salt to afford the corresponding 17.alpha.-ethynyl-17.beta.-hydroxy-9.alpha.-carbonate. This compound is then esterified with a novel series of reagents to give the 17-ester which can be reduced the corresponding 17-allene. Oxidation of this allene to the bis-epoxide compound, followed by treatment with an alkali metal salt of a carboxylic acid under phase transfer conditions gives 17.alpha.-hydroxy 21-ester 9.alpha.-carbonate. Elimination of the 9.alpha.-carbonate group affords the a 17.alpha.-hydroxy, 9(11)ene, which in a few subsequent steps can be converted to a variety of commercially important corticosteroids. Novel 9.alpha.-carbonate compounds are prepared in the various reaction steps.
Andrews David R.
Sudhakar Anantha R.
Schering Corporation
Swabey Ogilvy Renault
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