Methylphenidate (Ritalin) synthesis

Methylphenidate Take 1
 

    Methylphenidate, or Ritalin, is a common pharmaceutical used to treat ADHD. It is also commonly abused.

I did this synthesis two times over, so I'll start with my first idea. I'd also like to preface this with the fact that I am an amateur and I have not preformed this in the lab! I started from Styrene (the main precursor Styrofoam) which I would have reacted with mCPBA to achieve an epoxide. This would allow me to open the epoxide with a grignard. After opening the epoxide, I reacted with a decent oxidizing agent and did a fischer esterification. This was a good start but I could have eliminated a step.

Methylphenidate Take 2

So, for this one, I looked up the professional synthesis and that was my inspiration for this route. In their synthesis, they started with a nitrile but spent way too much time working with amides. They also spent some time playing around with the stereochemistry, but my synthesis does not require enantiopurity. This one was a pretty simple SN2 followed by a nitrile hydrolysis and an fischer esterification. I was pretty happy with this synthesis because it used simple reactions and only took three steps.

This was the professional synthesis (second image): https://en.wikipedia.org/wiki/Methylphenidate#Chemistry