Method for manufacturing diarylmethane compound

Patent metadata

Field	Value
Publication number	US-12018007-B2
Application number	US-201917058908-A
Country	US
Kind code	B2
Filing date	May 30, 2019
Priority date	May 31, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

An object is to provide a method for producing a compound which is useful as a synthetic intermediate for an active pharmaceutical ingredient of an antidiabetic drug or the like in an industrially inexpensive and efficient manner, and the present invention can achieve the object by reducing a compound (2) represented by the following formula (2):

wherein R 1 , Ar, n and X are as mentioned herein in the presence of a titanium compound by using a reducing agent to produce a compound (1) represented by the following formula (1):

wherein R 1 , Ar and n are the same as defined above.

First claim

The invention claimed is:

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

the method comprising the following steps (a) and (b):
(a) a step of providing a compound (2-1A) represented by the following formula (2-1A):

 and
(b) a step of reducing the compound (2-1A) in the presence of TiCl 4 by using an alkali metal borohydride salt to produce the compound (1A).

2. The production method according to claim 1 , wherein in the step (b), TiCl 4 and the alkali metal borohydride salt are added to a solvent to react the alkali metal borohydride salt with TiCl 4 at 20 to 120° C., followed by addition of the compound (2-1A) to the solvent.

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

the method comprising the following steps (a) and (b):
(a) a step of providing a compound (2-1A) represented by the following formula (2-1A):

 and
(b) a step of reducing the compound (2-1A) in the presence of a titanium compound by using an alkali metal borohydride salt to produce the compound (1A),
wherein:
the step (a) comprises a step of reacting a compound (4A) represented by the following formula (4A):

with a compound (5) represented by the following formula (5):

in the presence of a titanium compound to produce the compound (2-1A).

4. The production method according to claim 3 , wherein the titanium compound used in the step (b) is a titanium salt represented by the following formula (3):
TiR 3 r (OR 4 ) s   (3)

wherein
R 3 is a halogen atom,
R 4 is a substituted or unsubstituted C 1-6 alkyl group,
r and s are integers of 0 to 4 satisfying r+s=3 or 4,

or a solvate thereof.

5. The production method according to claim 3 , wherein in the step (b), the titanium compound and the alkali metal borohydride salt are added to a solvent to react the alkali metal borohydride salt with the titanium compound at 20 to 120° C., followed by addition of the compound (2-1A) to the solvent.

6. The production method according to claim 3 , wherein the titanium compound used in the step (a) is the titanium salt represented by formula (3) or a solvate thereof.

7. The production method according to claim 4 , wherein in the step (b), the titanium compound and the alkali metal borohydride salt are added to a solvent to react the alkali metal borohydride salt with the titanium compound at 20 to 120° C., followed by addition of the compound (2-1A) to the solvent.

8. The production method according to claim 4 , wherein the titanium compound used in the step (a) is the titanium salt represented by formula (3) or a solvate thereof.

9. The production method according to claim 5 , wherein the titanium compound used in the step (a) is the titanium salt represented by formula (3) or a solvate thereof.

10. The production method according to claim 7 , wherein the titanium compound used in the step (a) is the titanium salt represented by formula (3) or a solvate thereof.

Assignees

• Tokuyama Corp

Inventors

• Seki Masahiko

Classifications

• B01J2531/46

  Titanium · CPC title

• B01J2231/643

  of R2C=O or R2C=NR (R= C, H) · CPC title

• B01J31/0231

  Halogen-containing compounds · CPC title

• B01J27/135

  with titanium, zirconium, hafnium, germanium, tin or lead · CPC title

• A61P3/10 Primary

  for hyperglycaemia, e.g. antidiabetics · CPC title