The Hive => Tryptamine Chemistry => Topic started by: foxy2 on August 24, 2000, 07:26:00 PM
Title: Amide Reduction Alternatives
Post by: foxy2 on August 24, 2000, 07:26:00 PM
Hypothetically say one reacted 3-INDOLEACETIC ACID with dimethylamine to get the amide. Are there any ways of reduceing this amide without LAH, NaBH4 or other special reduceing agents that must be purchased via a chem supplier???
Thanks Foxy out
Title: Re: Amide Reduction Alternatives
Post by: terbium on August 24, 2000, 11:06:00 PM
I wish that sodium borohydride would work but I don't think so. I wonder what lithium in ammonia would do.
Title: Re: Amide Reduction Alternatives
Post by: Lilienthal on August 25, 2000, 04:47:00 AM
Foxy: 3-indoleacetic acid will not react with dialkylamines without further activation (e.g. with carbodiimides or as an acid chloride or anhydride).
Pure NaBH4 wouldn't work for reduction of amides. NaBH4 + activator (e.g. Lewis acids) will reduce amides, but will probably also reduce the indole to indoline (2,3-dihydroindole), at least to some extent. The same is true for borane BH3.
Terbium: Lithium (as well as sodium) in liquid ammonia is a strong base and will only reversibly deprotonate the indole (and maybe the alpha-CH2).
So LiAlH4 is the reagent of choice for amide reduction in this case. I'm not aware of other (practical) routes. Maybe there are some obscure bath tub methods... :)
Title: Re: Amide Reduction Alternatives
Post by: Rhodium on August 28, 2000, 05:03:00 AM