Production of pyrrolidine derivatives

Patent metadata

Field	Value
Publication number	US-10280140-B2
Application number	US-201715418889-A
Country	US
Kind code	B2
Filing date	Jan 30, 2017
Priority date	Jul 30, 2014
Publication date	May 7, 2019
Grant date	May 7, 2019

Abstract

The present invention relates to a method for the production of a pyrrolidine derivative.

First claim

What is claimed is:

1. A method for producing a pyrrolidine derivative, which comprises the following steps:
1) Incubating
(a) 5-oxo-pyrrolidine-2-carboxylic acid derivative of formula I

 wherein
R 1 is a linear alkyl residue with C 1 -C 6 ;
R 2 and R 3 are each independent from each other selected from the group consisting of:

with each:
n =0- 20,
X ═O or S,
and
(b) a compound selected from the group consisting of:
N-substituted diamine of formula II

where R 4 is a linear alkyl or acyl residue with C 2 to C 22 , and n =1-6; and
N-substituted monoamine of formula III

where R 5 is a linear alkyl or acyl residue with C 2 to C 22 ; and
N-substituted fatty amide of formula IV

where R 6 is a linear alkyl group with C 2 to C 24 ;
under appropriate reaction conditions to obtain a pyrrolidine derivative, and
2) Isolating the obtained pyrrolidine derivative.

2. The method of claim 1 , wherein any of the N-substituted diamine or N-substituted monoamine or N-substituted fatty amide comprises at R 4 or R 5 or R 6 any of a mono- or poly-unsaturated alkyl or acyl residue.

3. The method of claim 1 , wherein the 5-oxo-pyrrolidine-2- carboxylic acid derivative is a 5-oxo-pyrrolidine-2-carboxylic acid methyl ester of formula V

4. The method of claim 1 , wherein the N-substituted diamine is cocospropylene-1,3-diamine of formula VI:

5. The method of claim 4 , wherein the cocospropylene-1,3-diamine comprises approximately 70 mol-% of dodecylpropylenediamine and approximately 30 mol-% of tetradecylpropylenediamine.

6. The method of claim 1 , wherein the pyrrolidine derivative is glucoprotamin of formula VII:

7. The method of claim 1 , wherein the reaction conditions comprise an incubation temperature of approximately 60° C.

8. The method of claim 1 , wherein the reaction conditions comprise an incubation time of approximately 60 min.

9. The method of claim 1 , wherein the reaction conditions comprise a pressure of ≤ approximately 400 mbar.

10. The method of claim 1 , wherein a molar ratio of (a) to (b) is approximately 1 to approximately 1 up to approximately 1 to approximately 2.

11. The method of claim 1 , comprising removing reaction side products generated in step (1).

12. The method of claim 11 , wherein the reaction side product comprises methanol and the method comprises removing the methanol by distillation.

Assignees

• Univ Tuebingen Medizinische Fakultaet

Inventors

• Hirt Bernhard
• Zeyher Claus

Classifications

• C07D207/28 Primary

  2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles · CPC title