Posted by PA on March 08, 1997 at 19:01:27:
In Reply to: Re: ANDROSTENEDIOL REVISITED posted by Unique on March 08, 1997 at 16:48:41:
: : : 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