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Hexane → 17beta-Acetoxy-l-methyl-androsta-1,4-dien-3-one

HRID 259891
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 259891
C[Al](C)C.[CH3:5]CCCCC.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.[C:27]([O:30][C@H:31]1[CH2:36][CH2:35][C@H:34]2[C@H:37]3[C@H:47]([CH2:48][CH2:49][C@:32]12[CH3:33])[C@:45]1([CH3:46])[C:40](=[CH:41][C:42](=[O:50])[CH:43]=[CH:44]1)[CH2:39][CH2:38]3)(=[O:29])[CH3:28]>C(OCC)(=O)C.[Ni+2].C/C(/[O-])=C/C(C)=O.O>[C:27]([O:30][C@H:31]1[CH2:36][CH2:35][C@H:34]2[C@H:37]3[C@H:47]([CH2:48][CH2:49][C@:32]12[CH3:33])[C@:45]1([CH3:46])[C:40](=[CH:41][C:42](=[O:50])[CH:43]=[C:44]1[CH3:5])[CH2:39][CH2:38]3)(=[O:29])[CH3:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 102247Boldenone acetateHCID 16682925Trimethylaluminum

Produkt 1

HCID 1042750517beta-Acetoxy-l-methyl-androsta-1,4-dien-3-oneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 131719428
nickel(2+);(Z)-4-oxopent-2-en-2-olate
Katalysator
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

12 ml of trimethylaluminum of a 10% solution in hexane (12 mmol) is introduced at room temperature under nitrogen atmosphere. With stirring, 2.64 g of 2,6-di-tert-butyl-4-methylphenol is added in portions. The solution is stirred for 30 more minutes and 3.27 g (10 mmol) of 17β-acetoxy-androsta-l,4-dien-3-one in 20 ml of ethyl acetate is added at 25° C. The solution is heated to 60° C. and 143 mg of nickel(II)-acetylacetonate is added at 60° C. The solution is stirred for another 2.5 hours at this temperature. After cooling, 1.1 ml water is added for hydrolysis and stirred for 15 minutes. The solid is filtered off, rewashed twice-with 50 ml of ethyl, acetate. After concentration by evaporation of the ethyl acetate phases, a crude product is obtained, which is chromatographed on silica gel with hexane/ethyl acetate as eluent with increasing ethyl acetate portion. 1.55 g of initial material is recovered. 0.68 g of 17β-acetoxy-l-methyl-androsta-1,4-dien-3-one of melting point 144.1° C. is obtained. The yield is 20% of theory or 38% taking into consideration the initial material recovered.

Aufarbeitung

  1. additionis added at 25° C
  2. stirringThe solution is stirred for another 2.5 hours at this temperature
  3. temperatureAfter cooling
  4. stirringstirred for 15 minutes
  5. filtrationThe solid is filtered off
  6. concentrationAfter concentration
  7. customby evaporation of the ethyl acetate phases
  8. customa crude product is obtained
  9. customwhich is chromatographed on silica gel with hexane/ethyl acetate as eluent with increasing ethyl acetate portion
  10. custom1.55 g of initial material is recovered

Quellen und Nachweise

ORD-Eintrag
ord-2d2a04f0cfae4c46a518e861bbdb55fd
Quelldatensatz
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05523428

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