3-phenyl glutaric acid compound, preparation method and purpose thereof

A technology for phenylglutaric acid and compounds, which is applied in the application field of preparing pharmaceutical intermediates 1-indanone-3-acetic acid compounds (II), can solve high production costs, many synthesis steps, and cumbersome post-processing processes And other issues

Inactive Publication Date: 2012-03-21
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But the starting material of the above method - 4-formyl benzofuran compounds can be used in the following literature (1. Rois B. et al i>. J Chem Soc Perkin Trans 21984, (9): 1479-1485; 2. Willem AL. et al. Tetrahedron2005 , 61(32): 7746-7755; 3. Curt DH. et al. WO2003027090; 4. Bruce FM. et al. US2006111385; 5. Frank E. et al. WO9743272), but there are many synthesis steps and reaction Harsh conditions, cumbersome reaction operations and post-treatment processes, serious environmental pollution, low yields, high production costs and other disadvantages limit the large-scale preparation of 1-indanone-3-acetic acid compounds (II)

Method used

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  • 3-phenyl glutaric acid compound, preparation method and purpose thereof
  • 3-phenyl glutaric acid compound, preparation method and purpose thereof
  • 3-phenyl glutaric acid compound, preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Preparation of 3-(2,2-diethoxyethoxy)benzaldehyde (2a)

[0042] Add 12.21 g (0.1 mol) of 3-hydroxybenzaldehyde, 21.68 g (0.11 mol) of bromoacetal, anhydrous K 2 CO 3 16.56 g (0.12 mol) and N,N - 80 ml of dimethylformamide, heated to 120°C and stirred for 10 h, after the reaction was completed, filtered, the filtrate was evaporated to remove the solvent under reduced pressure, the residual oil was dissolved in 150 ml of chloroform, and successively washed with 10% aqueous sodium hydroxide solution 20 ml, washed with 25 ml of saturated NaCl aqueous solution, and the organic layer was washed with anhydrous NaCl 2 SO 4 Dry, filter, and evaporate the solvent under reduced pressure to obtain 22.87 g of 3-(2,2-diethoxyethoxy)benzaldehyde, with a yield of 96.0%; HR-TOFMS (+Q) m / z : 239.1280 ([C 13 h 18 o 4 +H] + Calculated: 239.1283).

Embodiment 2

[0043] Example 2 Preparation of 4-chloro-3-(2,2-diethoxyethoxy)benzaldehyde (2b)

[0044] Operation process is with embodiment 1, just 3-hydroxybenzaldehyde is replaced with 4-chloro-3-hydroxybenzaldehyde, N,N -Dimethylformamide was replaced by acetone, anhydrous K 2 CO 3 Replaced with sodium ethoxide, heated and refluxed and stirred for 20 h, followed by post-treatment in Example 1 to obtain 4-chloro-3-(2,2-diethoxyethoxy)benzaldehyde with a yield of 95.0%; HR-TOFMS ( +Q) m / z : 273.0898 ([C 13 h 17 ClO 4 +H] + Calculated: 273.0894).

Embodiment 3～15

[0045] Examples 3-15 Preparation of 3-(2-oxyethoxy)benzaldehyde compounds (2c~2o)

[0046] Operation process is with embodiment 1, just 3-hydroxybenzaldehyde is used corresponding compound ( 1 ) to replace bromoacetal with the corresponding 2-haloacetal, and change the reaction conditions accordingly to obtain 3-(2-oxyethoxy)benzaldehyde compounds ( 2c~2h ), and its chemical structure is as follows:

[0047]

[0048]

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Abstract

The invention discloses a 3-phenyl glutaric acid compound (I), and a preparation method thereof and application thereof to preparation of 1- indenone-3acetate compounds. In the formula, R1 and R2 respectively represent H, Cl, Br and I; R1 and R2 can be the same or not; R3 represents CH(OR4OR5)2; R4 and R5 represent C1-12 alkyl, or R4 and R5 are connected to form a ring.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry, and relates to 3-phenylglutaric acid compound (I), its preparation method and its application in the preparation of pharmaceutical intermediate 1-indanone-3-acetic acid compound (II), [0002] [0003] Where: R 1 , R 2 Each independently represents H, Cl, Br, I; R 1 , R 2 Can be the same or different; R 3 Indicates CH(OR 4 OR 5 ) 2 , R 4 , R 5 means C 1-12 Alkyl, or R 4 with R 5 connected to form a ring; X 1 -X 2 means CH 2 CH 2 , HC=CH. Background technique [0004] 1-indanone-3-acetic acid compound (II) is an important intermediate in the synthesis of ramelteon (Ramelteon), a selective melatonin receptor agonist developed by Takeda Pharmaceutical Company in Japan, 2005 It was listed in the United States for the first time in 2009, and it is used to treat insomnia with difficulty falling asleep, and it also has definite curative effect on chronic insomnia and short-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/64C07C27/02C07C51/377C07C51/363C07D319/06C07D317/22C07D307/77C07C47/575C07D307/79
Inventor 邓勇宋窈瑶强晓明程剑熊丽
Owner SICHUAN UNIV
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