The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: Vibrating_Lights on February 06, 2003, 05:52:00 AM

Title: Reduction of amides
Post by: Vibrating_Lights on February 06, 2003, 05:52:00 AM

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.
VL_

Title: Ac2O is needed
Post by: Rhodium on February 06, 2003, 09:19:00 AM

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.

Title: Red-Al or, possibly, sodium ...
Post by: Barium on February 06, 2003, 10:24:00 AM

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

Title: Sodium borohydride / acetic acid bears the...
Post by: Lilienthal on February 06, 2003, 10:56:00 AM

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.