Composition of matter

Patent metadata

Field	Value
Publication number	US-9637503-B2
Application number	US-201615186823-A
Country	US
Kind code	B2
Filing date	Jun 20, 2016
Priority date	Aug 7, 2012
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

The method relates to the field of asymmetric allylic amination and comprises preparing a chiral N-substituted allylic amine compound from the corresponding allylic substrates and substituted hydroxylamines, in the presence of a catalyst, said catalyst comprising copper compounds and a chiral ligand. Examples of chiral amine compounds which can be made using the method include Vigabatrin, Ezetimibe Terbinafine, Naftifine 3-methylmorphine, Sertraline, Cinacalcet, Mefloquine hydrochloride, and Rivastigmine. There are over 20,000 known bioactive molecules with chiral N-substituted allylic amine substructure. The method may also be used to produce non-natural chiral β-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of β-aminoacid ester which can be produced by the disclosed method, include, but are not limited to, N-(2-methylpent-1-en-3-yl)benzenamine and Ethyl 2-methylene-3-(phenylamino)butanoate. Further, the products of the method described herein can be used to produce chiral heterocycles and bioactive molecules or materials. A novel chiral copper-BINAM nitrosoarene complex is also set forth.

First claim

The invention claimed is:

1. A chemical compound having the formula [Cu(BINAM) 2 (ArNO) 2 ]OTf 2 .

2. The chemical compound of claim 1 wherein the compound is a chiral copper-BINAM nitrosoarene complex.

3. A chemical compound comprising:
a. a copper atom;
b. two nitrosoarenes;
c. two BINAM ligands;
d. two triflates.

4. The chemical compound of claim 3 wherein the compound is a chiral copper-BINAM-nitrosoarene complex.

5. The chemical compound of claim 3 wherein the copper-nitroso complex is chiral.

6. The chemical compound of claim 3 wherein at least one ligand is chiral.

7. The chemical compound synthesized from the process of combining copper triflate (Cu(OTf) 2 ), and R(+)-BINAM in the presence of toluene.

8. The chemical compound of claim 7 wherein the process comprises the steps of first creating a mixture of Cu(OTf) 2 , R(+)-BINAM, and toluene, stirring the mixture, and removing the solvent once a desired chemical compound is produced.

Assignees

• Univ Louisiana At Lafayette

Inventors

• Srivastava Radhey S
• Murru Siva

Classifications

• C07F1/005 Primary

  without C-Metal linkages · CPC title

• C07C209/02 Primary

  by substitution of hydrogen atoms by amino groups · CPC title

• C07C227/32

  by stereospecific synthesis · CPC title

• C07C209/68 Primary

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title

• C07B2200/07

  Optical isomers · CPC title