..... yep, both P/I2 and P/HI will ruin the methoxies....
didn't think of it bee4.
Putting them back would also bee problematic beecause of NH2 methylation. Of course, there's an amide protective group in midodrine (but not Methoxamine), but reduction of the OH will cleave it as well
Birch is an option, obviously - but it is much harder to do.
The best one could w/these things is probably to make them into BOX compounds - they also seem to bee quite worthwhile, as well as unexplored.
What i don't know is - how does one methylate aliphatic hydroxies? I know they're much harder to methylate - DMS doesn't do that, ordinarily.
If there was an easiysh way - then after the methylation/halogenation one would have an active comp'd! (In case Lugh's most valuable suggestion about amides being cleaved by the body works out)
So, dear chemical gurus, can you help?
Antoncho