Author Topic: internal ring closure/dehydration: phenylalanine  (Read 776 times)

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stratosphere

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internal ring closure/dehydration: phenylalanine
« on: January 13, 2004, 10:23:00 AM »
according to an article* i saw referenced in my chem book, beta-phenyl propanoic acid undergoes an internal ring closure/dehydration to yeild 1-indanone when treated with HF, i.e.

b-phenylpropanoic acid --HF-> 1-indanone

*fieser+hershberg, J. Am. Chem. Soc.,61,1272(1939)

if one were to assume that  N protonated phenylalanine (phenylalanine.HF) were to react in similiar manner as b-phenylpropanoic acid, this would be an interesting route to 2-amino-1-indanone, which would bare many similarities to cathinone.

any insight as to how the alpha NH3+ would effect the outcome of this reaction, or if it succeded, the cns activity of the resultant compound?