3,3-Di:alkoxy-androstanone prepn. in high yield

3,3-Di:alkoxy-androstanone prepn. in high yield

Prepn. of 3,3-dialkoxy-5alpha-androstane-17-diones of formula (I) from 5alpha-androstane-3,17-diones of formula (II) comprises mixing 1 mol. of (II) with 25-50 mol. of an alcohol of formula R1OH (III), 2.5-4.0 mol. of an orthoformate ester of formula HC(OR1)3 (IV) and 0.02-0.05 mol. p-toluenesulphon...

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Bibliographische Detailangaben
Hauptverfasser: MORALES R., MANUEL, ORIZABA, MX, RAMIREZ H., DANIEL, ORIZABA, MX, MEYER, MICHAEL, ORIZABA, MX, HAEUSER, HELMUT., ORIZABA, MX
Format: Patent
Sprache:eng ; ger
Schlagworte:
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
STEROIDS
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Zusammenfassung:Prepn. of 3,3-dialkoxy-5alpha-androstane-17-diones of formula (I) from 5alpha-androstane-3,17-diones of formula (II) comprises mixing 1 mol. of (II) with 25-50 mol. of an alcohol of formula R1OH (III), 2.5-4.0 mol. of an orthoformate ester of formula HC(OR1)3 (IV) and 0.02-0.05 mol. p-toluenesulphonic acid (pTSA); reacting for 1-12 hrs. at 15-40 deg.C. opt. with stirring; and working up conventionally. R1 = 1-4C alkyl (both R1 gps. being the same); R2 = H or Me. Also claimed is the prepn. of 17alpha-hydrocarbyl -17-beta-hydroxy-5alpha -androstan-3-one derivs. of formula (V), by preparing (I) from (II), reacting (I) with an organometallic cpd. of formula XR3 (VI) and cleaving the metal gp. in the prod. by hydrolysis. R3 = 1-6C opt. unsatd. aliphatic hydrocarbonyl; X = alkali metal or magnesium halide.