A CONVENIENT PROCEDURE FOR THEREDUCTION OF AMINOACIDS AND AMIDES USING TETRABUTYLAMMONIUM FLUORIDE AND POLYMETHYLHYDROSILOXANE

A range of alpha-aminoacids(1a-1h)have been converted efficiently to the corresponding beta-aminoalcohols: 2-amino-3-methylpentan-1-ol (isoleucinol) (2a), 2-amino-4-(methylthio)butan-1-ol (methioninol) (2b), 2-amino-3-methylbutan-1-ol (valinol) (2c), 2-amino-3-(4'-hydroxyphenyl) propan-1-ol (tyrosinol) (2d), 2-amino-3-phenylethan-1-ol (phenylglycinol) (2e), 2-amino-3-phenylpropan-1-ol (phenylalaninol) (2f), 2-aminoethan-1-ol (glycinol) (2g), and 2-aminopropanol-1-ol (alaninol) (2h), with polymethylhydrosiloxane, PMHS, in the presence of catalytic tetrabutylammonium fluoride, TBAF with > 61% yield. Carboxylic acids and their derivatives such as amides(3a and 3b) have also been reducedto the corresponding amines: N-ethylaniline(4a) and N-methylaniline(4b) with polymethylhydrosiloxane, PMHS, in the presence of catalytic tetrabutylammonium fluoride, TBAF with > 74% yield.