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

HRID 2052255Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

temperatureHeat
temperatureat reflux for 18 hours
filtrationfilter solids
customcrystallize from chloroform/hexane

Sources & evidence

ORD record: ord-4d72ea8ffee140d8805e2f915f730ea0
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04183924

Reaction notes

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