karlos³
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Yeast reduction of Isonitrosopropiophenone
Hello Dear fellow Mad Scientists,
I´ve prepared a small quantity of Isonitrosopropiophenone, from Propiophenone and n-butyl-nitrite, in dry EtOH with a small quantity of HCl(g)
dissolved in it.
The crystalline Material was precipitated as usual in the literature, with addition of cold water, and unreacted Propiophenone washed out from it
using Xylene.
The slightly yellow crystals have a satisfiying mp of 114°C, so I guess they are pure enough to use in further reactions.
So, what my question is: I have seen yeast reductions using both Azidopropiophenone, and also o-methyl-oximino propiophenone, as well as Reductions
with yeast of alpha-halopropiophenone.
Is it possible to reduce the ketone to an enantiomerically enriched (S) + Oximino-Alcohol?
Which is itself a Precursor to the aminoalcohol, 1S,2S-Norpseudoephedrine, no need to hide anything intended.
Which conditions would be desirable, with dried yeast wetted with a small amount of Water, to ensure enzyme activation? I guess actually living
fermenting yeast would be no good there?
Has the oxime to be made with methoxyhydroxylamine, or will an "normal" oxime also be reduced the same way on the alcoholic group as does the material
from my references?
Yeast Reduction of 1,2-Phenylpropandione-O-methyloxime
This is one of the papers im referencing to.
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karlos³
International Hazard
Posts: 1520
Registered: 10-1-2011
Location: yes!
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Mood: oxazolidinic 8)
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I need to update that thread.
It works, but one needs to use the water-soluble sodium salt of isonitrosopropiophenone.
The yield isn't great either, as the hydrolysis of the oxime(and thus reduction to the diol) is a competing reaction.
But then again, I only tried that once.
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