Vibrating_Lights (Hive Addict)
02-06-03 05:52
No 404947
      Reduction of amides  Bookmark   

If one was to have some 4-acetoxyindol-3-yl-N,N-diethylglyoxylamide what besides LAH would remove the =O to give the dialykated tryptamine.  Would a Clemmenson Zn/HCl do the trick. Or is that to harsh for the indole.  Is it also possible to add the acetoxy with GAA instead of AAnhydride.

He who holds the LSD holds the keys.
(Chief Bee)
02-06-03 09:19
No 405002
      Ac2O is needed  Bookmark   

Please do not open two threads about the synthesis of the same compound. But anyway, acetic acid is definitely not of any use to make the psilocin O-Acetyl ester.
(Hive Addict)
02-06-03 10:24
No 405020
      Red-Al or, possibly, sodium ...  Bookmark   

Red-Al or, possibly, sodium triacetoxyborohydride formed in situ from sodium borohydride and GAA.

02-06-03 10:56
No 405034
      Sodium borohydride / acetic acid bears the...  Bookmark   

Sodium borohydride / acetic acid bears the risk of reducing the indolic system to an indoline (2,3-doublebond hydrogenation).
As far as I know a Clemmenson reduction only reduces keto groups adjacent to aromatic rings, so if it  works, you would end up with the amide.