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Method of preparing 1,5-amino alcohol

An amino alcohol and phenyl technology, applied in the field of preparation 1, can solve the problems of harsh experimental conditions, cumbersome raw material synthesis, expensive reagents, etc., and achieves the effects of mild reaction conditions, cheap and easily available reagents, and large industrialization potential.

Active Publication Date: 2015-10-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generally speaking, the existing synthetic methods have disadvantages such as tedious synthesis of raw materials, expensive reagents, and harsh experimental conditions.

Method used

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  • Method of preparing 1,5-amino alcohol
  • Method of preparing 1,5-amino alcohol
  • Method of preparing 1,5-amino alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1, 4,5-diphenyl-5-(phenylamino)-1-pentanol (formula Ⅰ-a)

[0026]

[0027] Add N-benzylideneaniline (Formula II-a) (2mmol, 362mg), catalyst manganese dichloride (0.2mmol, 25mg), additive lithium chloride (3mmmol, 127mg), oxidant iodobenzene ( 4mmol, 816mg), solvent tetrahydrofuran (5mL) and phenylmagnesium bromide (formula III-a) (tetrahydrofuran solution, 1mol / L) (10mmol, 10mL), three-component reaction at room temperature. After 18h with saturated NaHCO 3 Solution (40mL) was used to quench the reaction, and then extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and spin-dried. 1 The diastereomeric ratio of 1,5-aminoalcohol (Formula I-a) in the crude product was detected by H NMR to be 1.3:1. The crude product was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 10 / 1, v / v) to obtain 583 mg of the target product (Formula I-a), with a yield of 88%.

[0028] The major d...

Embodiment 2

[0030] Example 2, 4-phenyl-5-(methylthiophenyl)-5-(phenylamino)-1-pentanol (formula Ⅰ-b)

[0031]

[0032] Add imine (formula II-b) (2mmol, 454mg), catalyst manganese diacetate (0.1mmol, 17mg), lithium chloride (3mmmol, 127mg), iodobenzene (3mmol, 612mg), tetrahydrofuran ( 9.3mL) and phenylmagnesium chloride (formula III-b) (tetrahydrofuran solution, 1.4mol / L) (8mmol, 5.7mL) at 0°C for a three-component reaction. After 24 h with saturated NaHCO 3 Solution (40mL) was used to quench the reaction, and then extracted with dichloromethane, and the organic phases were combined, dried with anhydrous sodium sulfate, filtered, and spin-dried. 1 The diastereomeric ratio of 1,5-aminoalcohol (Formula I-b) in the crude product was 1.4:1 by H NMR. The crude product was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 10 / 1, v / v) to obtain 718 mg of the target product (Formula I-b), with a yield of 95%.

[0033] The major diastereomers are characterized as fol...

Embodiment 3

[0035] Example 3, 4-phenyl-5-(4-chlorophenyl)-5-((2,4,6-trimethylphenyl)amino)-1-pentanol (Formula I-c)

[0036]

[0037] Add imine (Formula II-c) (2mmol, 516mg), catalyst manganese diacetylacetonate (0.1mmol, 25mg), lithium chloride (3mmmol, 127mg), iodobenzene (3mmol, 612mg), tetrahydrofuran into a 50mL flask in sequence (9.3mL) and phenylmagnesium chloride (formula III-b) (tetrahydrofuran solution, 1.4mol / L) (8mmol, 5.7mL) at 40°C for a three-component reaction. After 18h with saturated NaHCO 3 Solution (40mL) was used to quench the reaction, and then extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and spin-dried. 1 The diastereomeric ratio of 1,5-aminoalcohol (Formula I-c) in the crude product was determined to be 3.3:1 by H NMR. The crude product was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 10 / 1, v / v) to obtain 775 mg of the target product (Formula I-c), with a yield o...

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Abstract

The invention discloses a method of preparing 1,5-amino alcohol, wherein the method includes a following step of performing a three-component reaction to an imine represented as the formula II, a Grignard reagent represented as the formula III, a catalyst, an oxidation agent and an additive in a solvent to obtain the 1,5-amino alcohol which is represented as the formula I. The invention achieves simplified synthesis of the 1,5-amino alcohol, wherein the ratio of diastereoisomer of the 1,5-amino alcohol can reach 8:1 and the ratio can reach 99%. The raw materials are low in cost and easy to obtain. The method is mild in reaction conditions, is simple in operations and has an industrial production potential.

Description

technical field [0001] The present invention relates to a method for preparing 1,5-aminoalcohols. Background technique [0002] In organic synthesis, 1,5-aminoalcohols can be used as important intermediates, and many important piperidines can be obtained by intramolecular cyclization of 1,5-aminoalcohols. Therefore, 1,5-aminoalcohols are a class of compounds with important application value in the fields of industry, medicine, and agriculture. [0003] At present, the methods for preparing 1,5-aminoalcohols in organic synthesis mainly include the reductive coupling of imines and homoallyl alcohols, and the reduction of 2-piperidones. Generally speaking, the existing synthetic methods have disadvantages such as tedious synthesis of raw materials, expensive reagents, and harsh experimental conditions. Contents of the invention [0004] The object of the present invention is to provide a method for preparing 1,5-aminoalcohols. [0005] The method for preparing 1,5-aminoalc...

Claims

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Application Information

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IPC IPC(8): C07C215/28C07C215/38C07C217/60C07C213/00C07C323/32C07C319/20C07D333/20C07B49/00
Inventor 王从洋何若愚郑企雨黄志镗
Owner INST OF CHEM CHINESE ACAD OF SCI
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