[vegrunner9]

I'm trying to figure out a synthesis on paper but can't seem to find anything that will help. I have provided the synthesis along with what I have done so far.

I'm assuming you must start with a cyclic aldol reaction with a dehydration and then a conjugate addition to the double bond formed by the dehydration. There should only be one more step to convert the ketone to the amine that I want, but I just don't see a good way of doing it. I thought of converting it into a nitrile and then trying some other chemistry but that doesn't seem very efficient, also a Mannich reaction occurred to me but that wouldn't put the amine where I want it.

Any help would be greatly appreciated!

[jake.n]

I think the best way to do this would be a conjugate addition of acetone to your cyclohexenone (Stork enamine alkylation).  Following hydrolysis, you would get your diketone and reduction amination with ethylamine should give you your product.