Re: ANDROSTENEDIOL REVISITED


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Posted by Unique on March 09, 1997 at 23:15:27:

In Reply to: Re: ANDROSTENEDIOL REVISITED posted by PA on March 08, 1997 at 19:01:27:

: : : : QUESTION FOR THE PRO'S (UNIQUE,HULKSTER, ANIMAL ETC)
: : : : I saw the previous postings about conveting DHEA to
: : : : methandriol to methyltest. Did the recipe ever get
: : : : posted??? Inquring muscles want to know... Has anyone
: : : : had any success with the conversions?

: : :
: : : Maybe I have at one time. Methyl grignard reaction followed by hydrolysis and get rid
: : : of the excess unreacted ketone with semicarbazide HCl. Then oppenauer oxidation
: : : with Aluminium isopropoxide in toluene with cyclohexanone at reflux to get methyltest.
: : : Workup of the oppenauer reaction is not easy though.

: :
: : :
: : : PA

: : :
: : : if so where can
: : : : I get the post(recipe) Also, Would it be better to
: : : : prepare a DMSO solution of ANDOSTENE 50 instead of
: : : : ingesting it?

: : An alternative reaction would be to take DHEA, treat it
: : with trimethylsulphonium iodide, separate out the tetrhydropyranyl ether
: : via thin layer chromatography and reduce the latter via lithium
: : aluminum hydride to methandriol--which can be oxidized via oppenauer to
: : 17-meth. Of course, Pat's way of treating the DHEA with methylmagnesium
: : bromide is a little easier.
: : Keep up the fight
: : Unique

: No offense unique but your method makes little sense. Trimethylsulphonium iodide is not used
: to make tetrahydropyranyl ethers. And LAH will reduce the 17 ketone to a secondary alcohol.
: Where is the 17 methyl coming from? Or perhaps you meant methyl lithium instead of LAH?

: And I think you were thinking of androstenedione as the starting material. If the conjugated 3-ketone
: were protected (either as an enamine, enol ether etc.)then methyl lithium could be used to react at 17 C=O


:
: PA

Pat, what are you even talking about? The above is a very common way of producing both methandriol and
methytest. Methyllithium--HUH? Androstenedione--HUH? Dude, the trimethylsulphonium iodide will give
a mixture of 17B,20-eopxy-21-norpregn-5-en-3B-ol and its methyl ether--ie the tetrahydropyranyl. The ether
is reduced with LAH and then hydrolyzed (whoops, I missed this step, sorry!). It works and it's basic
organic, steroid chemistry.
Keep up the fight
Unique


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