Pyrrolidine compound

Patent metadata

Field	Value
Publication number	US-10040760-B2
Application number	US-201615566847-A
Country	US
Kind code	B2
Filing date	Apr 8, 2016
Priority date	Apr 21, 2015
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

In particular, an optically active substance of compound (III) can be produced by using compound (I) which is optically active.

First claim

The invention claimed is:

1. A compound represented by formula (1):

wherein Rf represents a C 1 -C 8 perfluoroalkyl group; R represents a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, a C 2 -C 13 alkoxycarbonyl group, a C 1 -C 12 fluorinated alkyl group, a nitro group, a cyano group or a halogen atom; and m represents an integer of 0 to 3.

2. The compound according to claim 1 , wherein the compound represented by formula (1) is optically active.

3. A method for producing a compound represented by formula (1):

wherein Rf represents a C 1 -C 8 perfluoroalkyl group; R represents a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, a C 2 -C 13 alkoxycarbonyl group, a C 1 -C 12 fluorinated alkyl group, a nitro group, a cyano group or a halogen atom; and m represents an integer of 0 to 3; comprising the steps of:
introducing a leaving group into a compound represented by formula (2):

wherein R and m are as defined above; and P G represents a protecting group for an amino group
to produce a compound represented by formula (3):

wherein X represents a leaving group; and R, m and P G are as defined above;
reacting compound (3) with ammonia to produce a compound represented by formula (4):

wherein P G , R and m are as defined above
or a salt thereof;
reacting compound (4) or a salt thereof with a C 1 -C 8 perfluoroalkanesulfonylating agent to produce a compound represented by formula (5):

wherein Rf, P G , R and m are as defined above; and deprotecting compound (5).

4. A method for producing a compound represented by formula (1):

wherein Rf represents a C 1 -C 8 perfluoroalkyl group; R represents a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, a C 2 -C 13 alkoxycarbonyl group, a C 1 -C 12 fluorinated alkyl group, a nitro group, a cyano group or a halogen atom; and m represents an integer of 0 to 3; comprising the steps of:
introducing a leaving group into a compound represented by formula (2):

wherein Rf and m are as defined above; and P G represents a protecting group for an amino group
to produce a compound represented by formula (3):

wherein X represents a leaving group; and R, m and P G are as defined above;
reacting the compound represented by formula (3) with trifluoromethanesulfonamide or a salt thereof to produce a compound represented by formula (5):

wherein Rf, P G , R and m are as defined above; and deprotecting compound (5).

5. A method for producing a compound represented by formula (III):

wherein R 1 represents a protecting group for a carboxyl group; and R 2 represents a protecting group for a hydroxyl group comprising the step of:
reacting a compound represented by formula (I):

wherein R 1 is as defined above
or a polymer thereof with a compound represented by formula (II):

wherein R 2 is as defined above
in the presence of a compound represented by formula (1):

wherein Rf represents a C 1 -C 8 perfluoroalkyl group; R represents a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, a C 2 -C 13 alkoxycarbonyl group, a C 1 -C 12 fluorinated alkyl group, a nitro group, a cyano group or a halogen atom; and m represents an integer of 0 to 3.

6. The method according to claim 5 , wherein the compound represented by formula (1) is an optically active form and an optically active form of the compound represented by formula (III) is produced.

7. A compound represented by formula (3a):

wherein R represents a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, a C 2 -C 13 alkoxycarbonyl group, a C 1 -C 12 fluorinated alkyl group, a nitro group, a cyano group or a halogen atom; m represents an integer of 0 to 3; and P G represents a protecting group for an amino group.

8. A compound represented by formula (5):

wherein R represents a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, a C 2 -C 13 alkoxycarbonyl group, a C 1 -C 12 fluorinated alkyl group, a nitro group, a cyano group or a halogen atom; m represents an integer of 0 to 3; P G represents a protecting group for an amino group; and Rf represents a C 1 -C 8 perfluoroalkyl group.

Assignees

• Sumitomo Chemical Co

Inventors

• Ikemoto Tetsuya
• Lutete Leopold Mpaka

Classifications

• C07C67/317

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups · CPC title

• C07D207/08

  with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms · CPC title

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C07D207/09 Primary

  Radicals substituted by nitrogen atoms, not forming part of a nitro radical · CPC title

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title