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Preparation method of (R)-N-benzyl-1-(4-methoxyphenyl) propan-2-amine

A technology of methoxyphenyl and benzyl, which is applied in the field of preparation of -N-benzyl-1-propan-2-amine, can solve the problems of low resolution yield and high production cost, and achieve the goal of reducing dangerous reagents Use, suitable for large-scale production, avoiding the effect of low yield of chiral resolution

Active Publication Date: 2022-05-10
武汉海特生物创新医药研究有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the lack of selectivity of this route, the resolution yield is too low, so the production cost is higher

Method used

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  • Preparation method of (R)-N-benzyl-1-(4-methoxyphenyl) propan-2-amine
  • Preparation method of (R)-N-benzyl-1-(4-methoxyphenyl) propan-2-amine
  • Preparation method of (R)-N-benzyl-1-(4-methoxyphenyl) propan-2-amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A synthetic route of (R)-N-benzyl-1-(4-methoxyphenyl)propan-2-amine disclosed by the present invention is as follows:

[0022]

[0023] Specific steps are as follows:

[0024] S1, the structural formula is Compound VI and S-methylbenzylamine carry out condensation reaction to obtain structural formula: Compound V, tetraethylorthosilicate and p-toluenesulfonic acid were added during the reaction.

[0025] The preparation steps of compound V are as follows: add S-methylbenzylamine (12.1g, 0.10mol), tetraethylorthosilicate (10.4g, 0.05mol), p-toluenesulfonic acid (0.76g, 0.004 mol) and 2-methyltetrahydrofuran (100mL), cooled with ice water until the internal temperature was less than 30°C, added p-methoxyphenylacetone (20.0g, 0.12mol) dropwise, heated to 90°C after the dropwise addition, and reacted 17 Hours, TLC (thin layer chromatography) control reaction is completed, cooled to 30 ° C, pad Celite filter, filter cake with 200mL of methyl tert-butyl ether, combine...

Embodiment 2

[0033] The difference between the preparation method disclosed in this example and Example 1 is that S-methylbenzylamine, tetraethylorthosilicate, p-toluenesulfonic acid and tetrahydrofuran are sequentially added in step S1.

Embodiment 3

[0035] The difference between the preparation method disclosed in this example and Example 1 is that in step S4, the free compound III is dissolved in methanol, and then benzaldehyde and palladium carbon are added.

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Abstract

The invention discloses a preparation method of (R)-N-benzyl-1-(4-methoxyphenyl) propan-2-amine, which sequentially comprises the following steps: carrying out condensation reaction on a compound VI and S-methylbenzylamine to obtain a compound V, carrying out heating reaction on the compound V obtained in the previous step in the presence of DBU to generate a compound IV, hydrolyzing, salifying with L-tartaric acid, and separating to obtain (R)-N-benzyl-1-(4-methoxyphenyl) propan-2-amine. The invention relates to a preparation method of (R)-N-benzyl-1-(4-methoxyphenyl) propane-2-amine, which comprises the following steps: adding a compound III into a potassium carbonate aqueous solution to obtain a free intermediate III, and carrying out reductive amination reaction on the free intermediate III and benzaldehyde to obtain (R)-N-benzyl-1-(4-methoxyphenyl) propane-2-amine, thereby reducing the use of dangerous reagents, avoiding the defect of low chiral resolution yield, and being suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical production, and in particular relates to a preparation method of (R)-N-benzyl-1-(4-methoxyphenyl)propan-2-amine. Background technique [0002] Formoterol (Formoterol) is a new type of β2-adrenergic receptor agonist developed by Japan Yamanouchi Company. In March 1986, its tablets were first launched in Japan for the treatment of chronic bronchial asthma, nocturnal asthma, exercise asthma, chronic obstructive pulmonary disease, and non-asthmatic respiratory diseases in children. Its synthetic route is as follows: [0003] [0004] (R)-N-benzyl-1-(4-methoxyphenyl)propan-2-amine is the key intermediate of formoterol, and its synthesis difficulty mainly lies in the introduction method of chiral carbon. [0005] Robert Hett reported the following route in the document Organic Process Research & Development 1998,2, 96-99: [0006] [0007] This route starts from p-methoxyphenylacetone, r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/60C07C213/00
CPCC07C213/00C07C249/02C07B2200/07C07C217/60C07C251/24C07C251/16
Inventor 李堃胡潇谦羊智成柴金柱
Owner 武汉海特生物创新医药研究有限公司
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