Chiral N-substituted allylic amine compounds

Patent metadata

Field	Value
Publication number	US-11021494-B2
Application number	US-201816211806-A
Country	US
Kind code	B2
Filing date	Dec 6, 2018
Priority date	Mar 27, 2017
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

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 13-aminoacid esters, a sub-class of chiral N-substituted allylic amine compounds. Examples of 13-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. An isolated chemical compound comprising: a. a copper atom; b. two nitrosoarenes; c. two nitrogen donor ligands; and d. two counterions.

2. The isolated chemical compound of claim 1 wherein the compound is a chiral coppernitrosoarene complex.

3. The isolated chemical compound of claim 1 wherein at least one ligand is chiral.

4. The isolated chemical compound of claim 1 wherein the copper atom is bonded to two chiral nitrogen-donor ligands.

5. The isolated chemical compound of claim 4 wherein the chiral nitrogen-donor ligands are selected from the group comprising BINAM and NOBIN.

6. The isolated chemical compound of claim 1 wherein the copper atom is bonded to two nitrosoarenes.

7. The isolated chemical compound of claim 6 wherein the nitrosoarenes consist of nitrosobenzene.

8. The isolated chemical compound of claim 1 wherein the copper complex is associated with at least one counter ion.

9. The isolated chemical compound of claim 8 wherein the at least one counter ion is selected from the group comprising triflates and halides.

Assignees

• Univ Louisiana At Lafayette

Inventors

• Srivastava Radhey S
• Murru Siva

Classifications

• B01J31/1805 Primary

  the ligands containing nitrogen · CPC title

• B01J31/2208

  Oxygen, e.g. acetylacetonates · CPC title

• C07F1/005

  without C-Metal linkages · CPC title

• C07F1/08 Primary

  Copper compounds · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title