Process for obtaining 6-alkylidenandrost-1, 4-diene-3-one

Details Process for obtaining 6-alkylidenandrost-1, 4-diene-3-one Process for obtaining 6-alkylidenandrost-1, 4-diene-3-one

C - Chemistry, Metallurgy

07

J

C07J 1/00 (2006.01)

Patent

CA 2708823

6-alkylidenandrost-1, 4-dien-3-ones of general formula (I), wherein R is H o alkyl; R1 y R2, independently of one another, represent H, OR3, OC(=O)R4 or O-(GPH), wherein R3 is H; C1-C6 alkyl or aryl; R4 is H or C1-C6 alkyl,; and GPH is a hydroxyl protecting group; or R1 and R2, together with the carbon atom to which they are bonded, form a carbonyl group or equivalent or a cyclic ketal; can be obtained by a process comprising subjecting the corresponding 6-alkyliden-4-androsten-3-one to a dehydrogenation reaction in the 1,2 position in the presence of a quinone, a silylating agent and a strong acid.

Les 6-alkylidènandrost-1,4-dién-3-ones répondant à la formule générale (I), dans laquelle R est H ou un alkyle ; R1 et R2, indépendamment l'un de l'autre, représentent H, OR3, OC(=O)R4 ou O-(GPH), où R3 est H ; un aryle ou un alkyle en C1-C6 ; R4 est H ou un alkyle en C1-C6 ; et GPH est un groupe protecteur d'hydroxyle ; ou R1 et R2, conjointement avec l'atome de carbone auquel ils sont liés, forment un groupe carbonyle ou équivalent ou un cétal cyclique ; peuvent être obtenues par un procédé consistant à soumettre la 6-alkylidèn-4-androstén-3-one correspondante à une réaction de déshydrogénation en position 1,2 en présence d'une quinone, d'un agent de silylation et d'un acide fort.

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