Method for preparing saturated potassium azacyclo-trifluoroborates

A technology of potassium trifluoroborate and potassium tetrahydropyrrole trifluoroborate, which is applied in the field of organic chemical synthesis, can solve the problems of difficult organic chemical reagents, unstable boric acid, and difficulty in preparation, and achieves simple and easy preparation process, Easy to commercialize product, good purity effect

Inactive Publication Date: 2015-04-01
成都安斯利生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of some saturated azacyclic organic boronic acids has certain difficulties, or their boronic aci

Method used

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  • Method for preparing saturated potassium azacyclo-trifluoroborates
  • Method for preparing saturated potassium azacyclo-trifluoroborates

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Preparation of N-tert-butylcarbonyltetrahydropyrrole:

[0022] In a 3L reaction flask, add 100g of tetrahydropyrrole (1.41mol), 1L of tetrahydrofuran and 8.58g of 4-dimethylaminopyridine (0.07mol), cool to 0°C, and slowly add 307.73g of tert-butylcarbonic anhydride (1.41mol) After the addition, it was raised to room temperature, reacted for 12 hours, added water to dilute, extracted with ether, separated, dried, and evaporated the solvent to obtain 221 g of N-tert-butylcarbonyl tetrahydropyrrole, with a yield of 92%, 1H NMR ( CDCl 3 ): 1.21ppm, unimodal (9H); 1.78ppm, multimodal (4H); 3.21ppm, multimodal (4H).

Embodiment 2

[0024] Preparation of N-tert-butylcarbamoylpiperidine:

[0025] In a 3L reaction flask, add 100g of piperidine (1.17mol), 1L of tetrahydrofuran and 7.17g of 4,4-dimethylaminopyridine (0.06mol), cool to 0°C, and slowly add 255.35g of tert-butylcarbonic anhydride (1.17mol ), the addition was completed, raised to room temperature, reacted for 12 hours, added water to dilute, extracted with ether, separated, dried, and evaporated the solvent to obtain 210 g of N-tert-butylcarbonylpiperidine, with a yield of 96%, 1H NMR ( CDCl 3 ): 1.26ppm, unimodal (9H); 1.45ppm, multimodal (4H); 1.68ppm, multimodal (2H); 13.18ppm, multimodal (4H).

Embodiment 3

[0027] Preparation of N-tert-butylcarbonyl-4-benzylpiperazine:

[0028] In a 5L reaction flask, add 150g N-tert-butylcarboylpiperazine (0.81mol), 107.04g benzyl chloride (0.85mol), 222.62g potassium carbonate (1.61mol) and 2L ethanol, heat to reflux for 12 hours, cool to At room temperature, filter, concentrate the solvent, add water to dilute, extract with dichloromethane, separate the organic phase, wash with water, dry, concentrate the solvent to obtain a crude product, recrystallize with n-hexane to generate N-tert-butylcarbonyl-4-benzyl Piperazine 190g, productive rate 85%, 1H NMR (CDCl 3 ): 141ppm, unimodal (9H); 2.40ppm, multimodal (4H); 3.21ppm, multimodal (4H); 3.26ppm, unimodal (2H); 7.28ppm, multimodal (5H).

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Abstract

The invention discloses a method for preparing saturated potassium azacyclo-trifluoroborates, which comprises the following steps: 1. reacting pyrrolidine and piperidine used as initial raw materials and tert-butyl carbonic anhydride to generate N-tert-butyl carbonyl pyrrolidine and N-tert-butyl carbonyl piperidine, and performing heating reflux on the N-tert-butyl carbonyl piperazine used as an initial raw material and benzyl chloride to generate N-tert-butyl carbonyl-4-benzyl piperazine; and 2. by means of the orientation effect of the N-tert-butyl carbonyl, in a nitrogen protective atmosphere, reacting with sec-butyl lithium at low temperature, then reacting with trimethylborate to generate saturated o-boric acid, adding a saturated KHF2 solution without separating the boric acid, and performing post treatment to respectively generate a potassium N-tert-butyl carbonyl-2-pyrrolidine trifluoroborate, a potassium N-tert-butyl carbonyl-2-piperidine trifluoroborate and a potassium N-tert-butyl carbonyl-4-benzyl-2-piperazine trifluoroborate. These saturated potassium azacyclo-trifluoroborates prepared by the invention are all white solids, are stable at room temperature in an air atmosphere, belong to very important organic chemical reagents and medical intermediate compounds, and have wide application prospects. The method disclosed by the invention is simple to operate, utilizes the cheap and accessible initial raw materials, achieves high yield and favorable purity, is easy to implement scale-up production, and realizes commercialized production.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing saturated azacyclic potassium trifluoroborate. Background technique [0002] Since many drug small molecules have saturated nitrogen-heterocyclic structures, how to efficiently construct these structures is challenging. If some saturated nitrogen-heterocyclic organic reagents (such as organic boronic acid reagents) can be found, it will undoubtedly provide a great solution to the above problems. help. However, the preparation of some saturated nitrogen-heterocyclic organic boronic acids has certain difficulties, or their boronic acids are unstable at room temperature and air conditions, so it is difficult to play the role of an organic chemical reagent. The present invention cleverly utilizes the ortho-positioning effect of tert-butylcarbonyl on the saturated azacyclic ring, and introduces boric acid at the ortho-position of nitrogen. Si...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 唐拥军莫珊刘玉琴
Owner 成都安斯利生物医药有限公司
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