Methanethiol → 17alpha-Methylthio-1,4-Androstadiene-3,11-Dione

HRID 2052255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2052255
[Na].[CH3:2][SH:3].CS(O[C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([C:26](=[O:28])[CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:29])[CH:21]=[CH:22]1)[CH2:17][CH2:16]3)(=O)=O>C(O)C>[CH3:2][S:3][C@@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([C:26](=[O:28])[CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:29])[CH:21]=[CH:22]1)[CH2:17][CH2:16]3

Komponenten

5

Edukt 3

HCID 878MethanethiolHCID 5360545SodiumHCID 5660910317beta-Methanesulfonyloxy-1,4-androstadiene-3,11-dione

Produkt 1

HCID 5435815917alpha-Methylthio-1,4-Androstadiene-3,11-Dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 6.9 gm. of sodium metal dissolved in 225 ml. of ethanol is added 30 ml. of methylmercaptan followed by 10 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione. Heat at reflux for 18 hours. Cool the solution to 0° C., filter solids and crystallize from chloroform/hexane to obtain the title compound; m.p. 180°-183° C.; [α]D26 +101.6° (DMF).

Aufarbeitung

  1. temperatureHeat
  2. temperatureat reflux for 18 hours
  3. filtrationfilter solids
  4. customcrystallize from chloroform/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4d72ea8ffee140d8805e2f915f730ea0
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04183924

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