Chemical process

Patent metadata

Field	Value
Publication number	US-2024190806-A1
Application number	US-202218552616-A
Country	US
Kind code	A1
Filing date	Mar 25, 2022
Priority date	Mar 26, 2021
Publication date	Jun 13, 2024
Grant date	—

Abstract

The present invention provides, inter alia, a process for producing a compound of formula (I) wherein the substituents are as defined in claim 1. The present invention further provides intermediate compounds utilised in said process, and methods for producing said intermediate compounds.

First claim

1 . A process for the preparation of a compound of formula (I) or a salt thereof:

wherein
R 1 is C 3 -C 7 cycloalkyl;
said process comprising:
reacting a compound of formula (II)

with a compound of formula (III)

wherein R 1 a is C 3 -C 7 cycloalkyl and X is halogen or hydroxy; or
R 1a is C 3 -C 7 cycloalkenyl and X is hydrogen;
in the presence of an acid to give a compound of formula (I).

2 . A process according to claim 1 , wherein R 1 is cyclopentyl or cyclohexyl.

3 . A process according to claim 1 , wherein a compound of formula (III) is selected from the group consisting of chlorocyclopentane, chlorocyclohexane, cyclopentanol, cyclohexanol, cyclopentene and cyclohexene.

4 . A process according to claim 1 , wherein R 1 is cyclohexyl and the compound of formula (III) is chlorocyclohexane or cyclohexanol.

5 . A process according to claim 1 , wherein the acid is a lewis acid.

6 . A process according to claim 5 , wherein the lewis acid is selected from the group consisting of aluminium(III) chloride, iron(III) chloride, titanium(IV) chloride, zirconium(IV) chloride and zirconium(IV) oxide chloride.

7 . A process according to claim 6 , wherein the lewis acid is aluminium(III) chloride.

8 . A process according to claim 1 , wherein the compound of formula (II) is used in an amount of at least 2 molar equivalents per mole of a compound of formula (III).

9 . A process according to claim 1 , wherein the compound of formula (II) is used in an amount of from 3 to 5 molar equivalents per mole of a compound of formula (III).

10 . A process according to claim 1 , wherein the acid is used in an amount of at least 1.1 molar equivalents per mole of a compound of formula (II).

11 . A process according to claim 1 , wherein the compound of formula (I) is further reacted with a compound of formula (IV),

wherein Y is a suitable leaving group and R 2 is hydrogen or C 1 -C 6 alkyl;
to give a compound of formula (V),

wherein R 1 is as defined in claim 1 and R 2 is as defined above.

12 . A process according to claim 11 , wherein Y is chloro.

13 . A process according to claim 1 , wherein the compound of formula (I) is further converted to a compound of formula (VI)

wherein R 1 is as defined in claim 1 .

14 . A process according to claim 11 , wherein the compound of formula (V) is further converted to a compound of formula (VI)

15 . A compound selected from the group consisting of a compound of formula (V-I), (V-II), (V-III) and (V-IV) below,

16 . Use of a compound of formula (I),

wherein R 1 is as defined in claim 1 , for preparing a compound of formula (VI).

Assignees

• Syngenta Crop Protection Ag

Inventors

• Staiger Roman
• Beaudegnies Renaud

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C2601/08

  the ring being saturated · CPC title

• C07C69/736 Primary

  the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C37/14

  by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond · CPC title