How to methylate alcohols (BOX series)?

[dennis_pro]

Hi, folks. I want to make some Shulgin's BOX-series substances. I have 2,5-dimethoxyphenylaminoethanol, prepared from Midodrine. How to methylate OH-group in this substance to produce 2,5,b-trimethoxyphenylethylamine?

And as alternative, how to reduct 2,5-dimethoxyphenylaminoethanol to produce 2C-H? J₂ with phosphorus will ruin methoxy groups

Thanks.
With best regards,
Dennis Prochko

[Antoncho]

Hey, Volk  This has been just recently discussed in the Novel Discourse - i think the thread just went down, it was called "Midodrine: an easy 3-step way to 2C-B" - go ahead, read it.

I also asked the question about methylation of alcohols - but, i'm sorry to say that, no one bothered to reply.    Maybee someone will answer your post ...

My congartulations on your joining The Hive - i promise, you're going to like this place!

Antoncho

P.S. Can i take your PGP-key and put it into the proper section of our forum? If you don't mind...

[Rhodium]

Shulgin's way of making the beta-alkoxy compounds is to add a sodium alkoxide to the corresponding nitrostyrene. Any alkylation that would alkylate an amino-alcohol would also alkylate the nitrogen.

[Antoncho]

Yeah, but in Midodrine the aminogroup is protected w/the amide function! So it shouldn't bee easily methylatable...

I can't believe noone on this board knows a single freaking way to methylate an aliphatic hydroxy!  Hey, dear chemists, can you lend us a hand? Please?

Antoncho