From: Maringanti Krishnamacharyulu (maringanti9$##$yahoo.com)
Date: Sat Feb 22 2003 - 09:35:20 EST
Hi!
The method that I had suggested will be useful only for the conversion of acid to alcohol. If you want to deoxygenate it further, you may have to use, sodium iodide and TMSCl in acetonitrile (in situ procedure for the generation of TMSI) and sodium borohydride. With a little bit of manipulation, you should be able to convert phenylalanine to the corresponding deoxygenated product in one pot. Thus, after the addition of Iodine in THF to a stirred suspension of phenylalanine and sodiumborohydride in THF at zerodeg. centegrade, wait for sometime, till you see complete conversion of acid to alcohol. You then add sodium Iodide as solid in portion (you need to dry it thoroghly) and TMSCl with syringe. You should probably take excess NaBH4 (I equivalent more). If you find the reaction sluggish in THF, then try leaching out THF from reaction mixture..add dry acetonitrile, and then, carryout your TMSI./NaBH4 mediated deoxygenation.
If TMSI does not help, another alternative is to use sulfurtrioxide and pyridine. If this also fails, try converting the acid into a tosylate or mesylate, and carryout NaBH4 reduction.
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