[Seanlet]

Doe anyone have a convenient route to oxidising the top compound cleanly back to the bottom compound? Since it's not something one would often see to do, it's not covered much by literature. The reason is 'green chemistry' in that rather than throw away the unwanted isomer, we want to oxidise it and use in bext batch (enamine then STAB).

Thanks in advance.

[Dan]

Maybe this (I don't have full text access):

http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201300007/abstract

A catalytic amount of Pd(OAc)₂ was successfully applied for the generation of enamines from various tertiary amines under oxidative conditions.

[camptzak]

I think you can convert to a secondary alcohol with H₃O⁺/H₂O then you can convert the secondary alcohol to a ketone using a couple different methods. heres a good one: http://en.wikipedia.org/wiki/Corey%E2%80%93Kim_oxidation

[orgopete]

Although I don't have access to a reaction database, this looks as though halogenation should occur on the nitrogen. A quaternary halo nitrogen should deprotonate with loss of the benzylic proton. A resulting iminium ion should hydrolysis to the ketone.