(11-beta)-17,17-Bis(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-one → 17-Ethylthio-9-fluoro-11beta-hydroxyandrosta-1,4,16-triene-3-one

HRID 839465Notes

Reaction equation

[CH2:1]([S:3][C:4]1(SCC)[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3)[CH3:2]>C(C1C=CC=CC=1CC)C>[CH2:1]([S:3][C:4]1[C@:5]2([CH2:22][C@H:21]([OH:23])[C@@:20]3([F:24])[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:25])[CH:14]=4)[C@@H:7]2[CH2:8][CH:9]=1)[CH3:6])[CH3:2]

Participants

Conditions

Temperature: 190 °C

Procedure

A suspension of 1.8 g of 17,17-bis(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4-dien-3-one in 120 ml of diethylbenzene is stirred at 190° C (oil bath temperature) for 1 hour. The solution is cooled to 0° C and the solid that precipitates is filtered. This is redissolved in 1:9 hexane-chloroform and chromatographed on a 60 g-silica gel column. Elution with 1:9 hexane-chloroform gives 1.35 g of a tlc-homogeneous material. Crystallization from chloroform-methanol gives 680 mg of the title compound, melting point 282°-283° C (dec.), with consistent spectral data.

Workup

temperatureThe solution is cooled to 0° C
customthe solid that precipitates
filtrationis filtered
dissolutionThis is redissolved in 1:9 hexane-chloroform
customchromatographed on a 60 g-silica gel column
washElution with 1:9 hexane-chloroform

Sources & evidence

ORD record: ord-c24764c8627e4d19ba30ae0d16e4d1b1
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04094840

Reaction notes

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