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l-dopa
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nubee
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Joined: 18 Feb 2005
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l-dopa

 Wed Apr 20, 2005 8:02 am		 Reply with quote
can anything be done from this...??

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CherrieBaby
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Joined: 01 Mar 2005
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 Wed Apr 20, 2005 11:09 pm		 Reply with quote
Take alpha-methyl-DOPA (aka methyldopa, Aldomet) instead.

(1) Decarboxylate the amino acid of alpha-methyl-DOPA to get 3,4-dihydroxy-phenylisopropylamine (aka dihydroxy-amphetamine)
(2) Turn the catechol into a methylenedioxy and you have MDA

I'm told you can't do rxn 2 because the amino will interfere with the methylenation. That you'd need to protect the amino before (2) and deprotect afterwards. I still can't understand why! Surely the phenol groups are acidic and undergo methylenation via a Williamson synth. The amino is basic, add alkali to it (as in the Williamson) and you don't get -NH(-). Add alkali to phenol and it gives -O(-)

Can someone tell me why alpha-methyl-DOPA to MDA won't go?
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