Acetylene → 17alpha-Ethynyl-17beta-hydroxy-16beta-methylandrosta-1,4,9(11)-trien-3-one

HRID 2290709

Reaktionsgleichung

Reaktionsgleichung von HRID 2290709
C#C.[CH:3](NC(C)C)(C)[CH3:4].C#C.C1COCC1.C([Li])CCC.[CH3:22][C@H:23]1[CH2:28][C@H:27]2[C@H:29]3[C:39](=[CH:40][CH2:41][C@:25]2([CH3:26])[C:24]1=[O:43])[C@:37]1([CH3:38])[C:32](=[CH:33][C:34](=[O:42])[CH:35]=[CH:36]1)[CH2:31][CH2:30]3>C1COCC1>[C:3]([C@:24]1([OH:43])[C@@H:23]([CH3:22])[CH2:28][C@H:27]2[C@H:29]3[C:39](=[CH:40][CH2:41][C@:25]12[CH3:26])[C@:37]1([CH3:38])[C:32](=[CH:33][C:34](=[O:42])[CH:35]=[CH:36]1)[CH2:31][CH2:30]3)#[CH:4]

Komponenten

7

Edukt 5

HCID 6326AcetyleneHCID 7912DiisopropylamineHCID 13518558HCID 13518558, VerbindungHCID 67285190acetylene THFHCID 178418339Butyllithium

Produkt 1

HCID 8674017617alpha-Ethynyl-17beta-hydroxy-16beta-methylandrosta-1,4,9(11)-trien-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Dry THF (5 l) is cooled to -20° and acetylene (0.27 kg) is dissolved in the THF at -20°. Diisopropylamine (880 ml) is added to the acetylene/THF solution. n-Butyllithium (1.6M, 3.88 l) is added to the mixture maintaining the temperature at -20° and stirred for 30 min. 16β-Methylandrosta-1,4,9(11)-triene-3,17-dione (IB) in (THF) is added to the reaction mixture at or below -20° and stirred for 20 min to give the title compound.

Aufarbeitung

  1. temperaturemaintaining the temperature at -20°
  2. stirringstirred for 20 min

Quellen und Nachweise

ORD-Eintrag
ord-75b00166997b4d7cb807282f56dc8d9e
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618456

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