Amine-boranes bearing borane-intolerant functionalities

Patent metadata

Field	Value
Publication number	US-9988402-B2
Application number	US-201715680259-A
Country	US
Kind code	B2
Filing date	Aug 18, 2017
Priority date	Aug 19, 2016
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

Disclosed herein is the preparation of functional group containing amine-boranes from the corresponding amines. The mild reaction conditions allow for the direct preparation of several hitherto inaccessible amine-boranes containing a functional moiety, such as but not limited to, alkene, alkyne, hydroxyl, thiol, acetal, ester, amide, nitrile, nitro, and alkoxysilane.

First claim

What is claimed is:

1. A process for preparing an amine-borane, comprising the steps of
a. preparing about two equivalents of sodium borohydride and about four equivalents of sodium bicarbonate;
b. adding about one equivalent of an amine, wherein said amine comprises a functional group selected from the group consisting of alkene, alkyne, nitro, hydroxyl, thiol, cyano (nitrile), acetal, ester, amide, and alkoxysilane;
c. adding THF (tetrahydrofuran) while stirring to afford a reaction mixture of said amine in a concentration of about 0.5˜2 M (moles/liter);
d. adding about 3-4 equivalents of water in a THF solution dropwise to the reaction mixture of step c under vigorous stirring; and
e. stirring for about 4 to 48 hours to afford an amine-borane, wherein said amine-borane comprises a functional group selected from the group consisting of alkene, alkyne, nitro, hydroxyl, thiol, cyano (nitrile), acetal, ester, amide, and alkoxysilane.

2. The process of claim 1 , wherein the water-THF solution is about 14% (v/v) water in THF.

3. The process of claim 1 , wherein said amine is a monoamine or a diamine.

4. The process of claim 1 , wherein said process is performed at an ambient temperature.

5. The process of claim 1 , wherein said amine-borane is part of an aromatic molecule, an aliphatic molecule, or a combination thereof.

6. The process of claim 1 , wherein said amine-borane is part of a cyclic structure, a linear structure, a branched structure, or a combination thereof.

7. The process of claim 1 , wherein said water in a THF solution is about four equivalents of said amine when said amine comprises a functional group selected from the group consisting of alkene, alkyne, nitro, hydroxyl, thiol, cyano (nitrile), acetal, ester, amide, and alkoxysilane.

8. The process of claim 1 , wherein said amine comprises two or more functional groups selected from the group consisting of alkene, alkyne, nitro, hydroxyl, thiol, cyano (nitrile), acetal, ester, amide, and alkoxysilane.

9. The process of claim 1 , wherein said amine-borane comprises two or more functional groups selected from the group consisting of alkene, alkyne, nitro, hydroxyl, thiol, cyano (nitrile), acetal, ester, amide, and alkoxysilane.

Assignees

• Purdue Research Foundation

Inventors

• Ramachandran P Veeraraghavan
• Kulkarni Ameya Sanjay

Classifications

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C01B35/146

  Compounds containing boron and nitrogen, e.g. borazoles (ammonium tetrafluoborates C01B35/063; ammonium borates C01B35/12) · CPC title

• C07F5/022 Primary

  without C-boron linkages · CPC title

• C07F7/1848

  Chemistry & Metallurgy · mapped topic