Preparation of secondary amines with electrophilic N-linchpin reagents

Patent metadata

Field	Value
Publication number	US-11767291-B2
Application number	US-201816614272-A
Country	US
Kind code	B2
Filing date	May 17, 2018
Priority date	May 17, 2017
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identical groups. Also provided herein are compositions for use in the preparation of the secondary amine.

First claim

What is claimed is:

1. A compound of the formula:

wherein:
X 1 and X 2 are each independently C, S, or S(O);
R 1 and R 2 are each isopropoxy; and
R 3 is a leaving group, wherein the leaving group is selected from the group consisting of halo, alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , and substituted arylsulfonyloxy (C≤12) ;

or a salt thereof.

2. The compound of claim 1 , wherein the compound is further defined as:

wherein:
R 1 and R 2 are isopropoxy; and
R 3 is a leaving group, wherein the leaving group is selected from the group consisting of halo, alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , and substituted arylsulfonyloxy (C≤12) ;

or a salt thereof.

3. The compound of claim 1 , wherein R 3 is a leaving group is selected from the group consisting of alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , and substituted arylsulfonyloxy (C≤12) .

4. The compound of claim 1 , wherein X 1 and X 2 are C.

5. The compound of claim 1 , wherein the compound is further defined as:

or a salt thereof.

6. The compound of claim 5 , wherein the compound is:

or a salt thereof.

7. The compound of claim 1 , wherein the compound is further defined as:

wherein:
R 1 and R 2 are each isopropoxy; and
R 3 is a leaving group, wherein alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , or substituted arylsulfonyloxy (C≤12) ;

or a salt thereof.

8. The compound of claim 7 , wherein R 3 is arylsulfonyl (C≤12) or substituted arylsulfonyl (C≤12) .

9. The compound of claim 7 , wherein R 3 is alkylsulfonyloxy (C≤12) or substituted alkylsulfonyloxy (C≤12) .

10. The compound of claim 7 , wherein R 3 is arylsulfonyloxy (C≤12) or substituted arylsulfonyloxy (C≤12) .

11. The compound of claim 10 , wherein R 3 is arylsulfonyloxy (C≤12) .

Assignees

• Univ Rice William M

Inventors

• Kattamuri Padmanabha Venkatesh
• Kurti Laszlo

Classifications

• C07C311/19 Primary

  to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups · CPC title

• C07C69/36

  Oxalic acid esters · CPC title

• C07C69/675

  of saturated hydroxy-carboxylic acids · CPC title

• C07C227/06

  by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid · CPC title

• C07C381/00

  Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00 · CPC title