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1, 4/1, 5-amino alcohol compound and preparation method thereof

A compound and amino alcohol technology, applied in 1 field, can solve the problems of many side reactions, dangerous reagents, unstable reagents, etc., and achieve the effect of simple route, high yield and simple reaction conditions

Inactive Publication Date: 2020-10-16
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These known methods all have different degrees of limitations such as unstable reagents, difficulty in amplification, many side reactions, and dangerous reagents.

Method used

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  • 1, 4/1, 5-amino alcohol compound and preparation method thereof
  • 1, 4/1, 5-amino alcohol compound and preparation method thereof
  • 1, 4/1, 5-amino alcohol compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of compound 4Aa

[0024] Under the protection of argon, compound 3A (100mg, 0.53mmol) was dissolved in dry tetrahydrofuran (3mL), and the newly prepared o-methylbenzylzinc bromide reagent (2.14mL, 1M in THF, 4eq .) and trimethylchlorosilane (0.14mL, 2eq.), after 12 hours of reaction, 1N HCl (0.6mL) was added to the reaction system, the system was placed in an ice bath and stirred for 15min, diluted with water, and warmed to room temperature, acetic acid Extracted with ethyl ester (5mL×3), combined the organic phases, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated by filtration, and the residue was subjected to silica gel column chromatography (PE / EA=2:1) ​​to obtain white solid compound 4Aa (123mg, 79%). 1 H NMR (400MHz, CDCl 3 , rotamers) δ7.17-7.09 (m, 4H), 4.55-4.34 (m, 1H), 3.91-3.69 (m, 1H), 3.66-3.59 (m, 2H), 2.81-2.70 (m, 2H), 2.34(s, 3H), 1.98(s, 1H), 1.69-1.54(m, 3H), 1.46-1.30(m, 10H)ppm.

[0025] Compounds 4Ab~...

Embodiment 2

[0085] Synthesis of compound 4Aa

[0086] Under the protection of argon, compound 3A (100mg, 0.53mmol) was dissolved in dry tetrahydrofuran (3mL), and the newly prepared benzyl zinc bromide reagent (2.14mL, 1M in THF, 4eq.) was slowly added dropwise at -78°C and Trimethylsilyl trifluoromethanesulfonate (0.19mL, 2eq.), after reacting for 12 hours, 1N HCl (0.6mL) was added to the reaction system, the system was placed in an ice bath and stirred for 15min, diluted with water, and warmed to room temperature , extracted with ethyl acetate (5mL×3), combined the organic phases, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated, and the residue was subjected to silica gel column chromatography (PE / EA=2:1) ​​to obtain white solid compound 4Aa ( 123 mg, 79%).

Embodiment 3

[0088] Synthesis of compound 4Aa

[0089] Under the protection of argon, compound 3A (100mg, 0.53mmol) was dissolved in dry tetrahydrofuran (3mL), and the newly prepared benzyl zinc bromide reagent (2.14mL, 1M in THF, 4eq.) was slowly added dropwise at -78°C and Boron trifluoride diethyl ether (0.14mL, 2eq.), after 12 hours of reaction, 1N HCl (0.6mL) was added to the reaction system, the system was placed in an ice bath and stirred for 15min, diluted with water, and raised to room temperature, extracted with ethyl acetate (5mL×3), the organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated by filtration, and the residue was subjected to silica gel column chromatography (PE / EA=2:1) ​​to obtain white solid compound 4Aa (123mg, 79%) .

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Abstract

The invention belongs to the field of chemical synthesis, and relates to a new 1, 4 / 1, 5-amino alcohol compound and a preparation method thereof. The 1, 4 / 1, 5-amino alcohol compound synthesized by the method has a structure shown as the following formula in the specification. The technical route for preparing the 1, 4 / 1, 5-amino alcohol compound is simple in reaction condition, conicse in route and relatively high in yield, the used reagents are common reagents, and the method has the characteristics of high efficiency, low cost, compatibility with various functional groups, capability of realizing amplified preparation and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a new 1,4 / 1,5-aminoalcohol compound and a preparation method thereof. Background technique [0002] 1,4 and 1,5-aminoalcohols have amino and hydroxyl key functional groups, which can interact with life-related biomacromolecules in vivo, and thus become key intermediate fragments of many natural products and drug molecules. It is widely used as a synthetic building block in organic synthesis and as a ligand compound in the field of organic catalysis. For example, the structures of 1,4 and 1,5-aminoalcohols can be easily converted into the versatile synthetic building blocks of pyrrole amide and piperidine amide in chemical drugs and the more versatile multifunctionalized furan derivative fragments through oxidation, while It can also be used as a ligand to catalyze the asymmetric addition reaction of organozinc and carbonyl. However, the preparation methods of 1,4 / 1,5-a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/16C07C271/22C07C269/06C07D307/22
CPCC07C271/16C07C271/22C07C269/06C07D307/22C07C2601/14Y02P20/55
Inventor 魏邦国王雪梅司长梅汪晨周祝
Owner FUDAN UNIV
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