Sciencemadness Discussion Board

protection of one of the two ketone sites

chemrox - 1-11-2012 at 20:56

Piperidione, 3,3-diethylpiperidine-2,4-dione, CAS 77-03-2, has two oxo groups. The molecule is almost bilaterally symmetrical, but not quite. One of the two oxo's is adjacent to a piperidyl N. What I would like to do is perform reductive ams with different amines on both oxos or a reductive am on one and maybe a Grignard to the other. Anyway, in order to be able to treat these separately it will be necessary to protect one of the oxos. I'm asking if this is feasible and whether the placement of one of them adjacent to the secondary amine helps make this possible?

DJF90 - 1-11-2012 at 21:31

The carbonyl in the 2-position is part of the amide functionality. As such it will be much less reactive towards nucleophiles than the 4-one.