tremorine

Priscila: This synthesis looks elegant and simple. It makes good sense. It looks like chemsketch wants to turn your nitrogens into sodiums, but I understand what you are trying to do here. Nice work. Bruce Bondurant

Ryan Carbaugh Tremorine



Ryan: I like your method of using enamine chemistry to build the carbon skeleton of the pyrrolidine ring. The zinc amalgam reduction is really neat too. I think you may be missing a carbon in the final product What you really need is 1,4-dibromy-2-butyne. The pyrrolidine would react with this like a shot. and give you your final product. Bruce Bondurant

Dr. Bondurant, I have fixed the problem. Just replace what I have synthesized below with the dibromoacetylene above.

Ryan: This works. I think you have a winner here. Bruce Bondurant

Type in the content of your page here. Katalin Sagi (extra credit)

Katalin: I like your strategy, especially your method for forming the pyrrolidine ring. It is a nice use of the chemistry that we have studied. I am a little concerned about reacting 3-chloropropyne with sodium amide. Because the chloro next to the alkyne is more reactive than the dichloromethane, you may end up with a polymer. One solution may be to pour the di-anion of the acetylene into an excess of dichloromethane. Another way would be to react with methoxymethylchloride aka MOM chloride. it is CH3OCH2Cl. This would give you the protected alcohol. Then there are a number of ways to remove methyl ether. Then you can replace it with bromine, using PBr3 or CBr4 and triphenylphosphine Bruce Bondurant

[|ether removal]

Correction of Compound Tremorine:

Katalin: I think this would work well. There may be a little problem with cooking it with HBr, because of the reactivity of the triple bond, but it is clear that from your reference that there are several ways to take off an ether. The reference that refers to trimethyl silyl iodide, also works with methyl ethers, and would be more gentlethis. If an HBr cleavage were to work, it would probably put on a bromide in in that step, without the necessity of PBr3. This is a nice synthesis. Bruce Bondurant (extra credit - Tremorine) Alfred Rush