Newsgroups: alt.drugs.chemistry
From: [e--u--s] at [netcom.com] (Eleusis)
Subject: Re: *ZWITTERION* - MDP-2-Pol from Safrole via H2SO4 Oxidation
Date: Wed, 14 Feb 1996 15:33:49 GMT

In article <[101315 Z 14021996] at [anon.penet.fi]>, [an 216208] at [anon.penet.fi] wrote:

>Anyway, the total yield of product, 3,4-methylenedioxyphenyl-2-propanol, 
>was 72.0g, which comes out to a percent yield of 81%. Not bad for being
>intentionally sloppy, huh?
>
>Yes kids, I just converted plain old safrole to the secondary alcohol in
>under 4 hours total time with a percent yield of 81%, and I can only 
>expect it to get better with more careful attention to detail next time 
>and a more thorough extraction of the aqueous reaction matrix. Going from 
>here to the ketone is a breeze, but at least one person (DrH) is a 
>proponent of direct reductive amination starting from the alcohol.

Hmmm... good work, and finally a bit of vindication to my near-rabid belief 
that it could be pulled off. I had just about given up on the idea, too.

Ancillary details at this point are in order, I suppose...

o Being an alcohol, this compound will probably have a better shelf
  life than the ketone.

o Oxidation to the ketone can be accomplished with a bewildering array of
  techniques, including, but not limited to the following:
  1) Jone's reagent (CrO3+H2SO4+MeCOMe)
  2) Pool chlorinating solution & gl. AcOH (details in the future)
  3) Potassium permanganate adsorbed on zeolite (details)
  4) Potassium Dichromate with quaternary ammonium salt & H2SO4 (details)

o Oxidation to the ketone may not even be necessary, if the Mitsunobu
  reaction can be implemented here (using triphenylphosphine to prepare
  the -OH for nucleophilic attack). This is the method that DrH is a
  fan of and may give excellent amination yields with mild conditions
  and quick reaction times.

All in all, a surprising gem has been presented here, but I can't help 
wonder how many people will actually get anything useful out of it... Kudos 
to the anon contributor who helped you out.



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