Chiral N-substituted allylic amine compounds
US-11021494-B2 · Jun 1, 2021 · US
Chiral N-substituted allylic amine compounds
US12129268B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-12129268-B2 |
| Application number | US-202117239991-A |
| Country | US |
| Kind code | B2 |
| Filing date | Apr 26, 2021 |
| Priority date | Jan 30, 2015 |
| Publication date | Oct 29, 2024 |
| Grant date | Oct 29, 2024 |
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- Title
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Abstract
Official abstract text for this publication.
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 ß-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of ß-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
Opening claim text (preview).
The invention claimed is: 1. A chemical compound made by a process comprising combining Cu(X) 2 and R(+)-BINAM, wherein X is triflate, to give [Cu(BINAM) 2 OTf 2 and combining the [Cu(BINAM) 2 OTf 2 with N,N-diethyl-4-nitrosoaniline. 2. The chemical compound of claim 1 , wherein the N,N-diethyl-4-nitrosoaniline coordinates with the copper atom of the chemical compound through the oxygen atom of the N,N-diethyl-4-nitrosoaniline.
Assignees
Inventors
Classifications
Oxygen, e.g. acetylacetonates · CPC title
without C-Metal linkages · CPC title
- B01J31/1805Primary
the ligands containing nitrogen · CPC title
Copper · CPC title
Optical isomers · CPC title
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- What does patent US12129268B2 cover?
- 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, Ezeti…
- Who is the assignee on this patent?
- Univ Louisiana At Lafayette
- What technology area does this patent fall under?
- Primary CPC classification B01J31/1805. Mapped technology areas include Operations & Transport.
- When was this patent published?
- Publication date Tue Oct 29 2024 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 6 related publications on this page (citations in our corpus or others sharing the same primary CPC).