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A kind of synthetic method of 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine-6-carboxylic acid

A technology of tert-butoxycarbonyl and octahydrofuran is applied in the field of synthesis of 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine-6-carboxylic acid, and can solve the problem of not being suitable for industrial synthesis methods, etc., to achieve the effects of convenient operation, easy reaction and high yield

Active Publication Date: 2018-05-04
WUXI APPTEC (TIANJIN) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Example 1: Compound 1 (7.11 g, 51.1 mmol) was dissolved in ethanol (300 mL), and after adding thionyl chloride (36 mL) dropwise at room temperature, the reaction was refluxed overnight. TLC (ethyl acetate=1, R f = 0.8) shows that the reaction is complete, the reaction mixture is spin-dried under reduced pressure, and the residue is added to a saturated aqueous sodium carbonate solution to make pH=7 to obtain compound 2, which is directly used in the next step.

[0012] The solution of Compound 2 was added to water (150 mL), sodium carbonate (7.33 g, 0.307 mol) and iodine (9.65 g, 0.153 mol) were added, and the reaction was carried out at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f = 0.8) showed that the reaction was complete, and the reaction solution was added with 1N hydrochloric acid to make the pH=7 to precipitate a solid, which was filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (9.3 ...

Embodiment 2

[0022] Example 2: Compound 1 (71.1 g, 511 mmol) was dissolved in ethanol (1500 mL), and after adding thionyl chloride (360 mL) dropwise at room temperature, the reaction was refluxed overnight. TLC (ethyl acetate=1, R f = 0.8) shows that the reaction is complete, the reaction mixture is spin-dried under reduced pressure, and the residue is added to a saturated aqueous sodium carbonate solution to make pH=7 to obtain compound 2, which is directly used in the next step.

[0023] The solution of Compound 2 was added to water (1500 mL), sodium carbonate (73.3 g, 3.07 mol) and iodine (96.5 g, 1.53 mol) were added, and reacted at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f = 0.8) showed that the reaction was complete, and 1N hydrochloric acid was added to the reaction solution to make the pH=7 to precipitate a solid, which was filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (93.3 g), with a yield of 82...

Embodiment 3

[0033] Example 3: Compound 1 (711 g, 9.11 mol) was dissolved in ethanol (5 L), and thionyl chloride (3.6 L) was added dropwise at room temperature, and the reaction was refluxed overnight. TLC (ethyl acetate=1, R f = 0.8) shows that the reaction is complete, the reaction mixture is spin-dried under reduced pressure, and the residue is added to a saturated aqueous sodium carbonate solution to make pH=7 to obtain compound 2, which is directly used in the next step.

[0034] The solution of Compound 2 was added to water (15 L), sodium carbonate (733 g, 30.7 mol) and iodine (965 g, 15.3 mol) were added, and the reaction was carried out at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f = 0.8) showed that the reaction was complete, and 1N hydrochloric acid was added to the reaction solution to make the pH=7 to precipitate a solid, which was filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (925 g), with a y...

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Abstract

The invention relates to a synthesis method of 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine-6-carboxylic acid, and mainly solves the technical problem that there is no suitable industrial synthesis method at present. The present invention is divided into six steps, firstly, compound 2 is obtained by esterification of compound 1, then compound 3 is obtained by reacting with iodine, compound 4 is obtained after acetylation of compound 3, compound 5 is obtained by coupling again, compound 6 is obtained by ring closure, and compound 6 is obtained by hydrogenation 7, and then reacted with Boc anhydride to obtain compound 8, which was hydrolyzed to obtain the final compound 9. The reaction formula is as follows: .

Description

technical field [0001] A method for synthesizing the compound 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine-6-carboxylic acid (CAS: 1314388-60-7) involved in the present invention. Background technique [0002] The compound 4-(tert-butoxycarbonyl)octahydrofuro[3,2-b]pyridine-6-carboxylic acid and related derivatives are widely used in medicinal chemistry and organic synthesis, and are well sold in the market. Currently, the synthesis of 4-(tert-butoxycarbonyl)octahydrofuro[3,2-b]pyridine-6-carboxylic acid is difficult. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of this invention is to develop a kind of raw material that is easy to get, easy to operate, easy to control the reaction, and a higher yield of 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/048
Inventor 邢少廷于涵张金宝赵东邱继平刘洋朱喜雯马坤艳陈远丽靳爱杰袁晓斌于凌波何振民马汝建
Owner WUXI APPTEC (TIANJIN) CO LTD
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