Synthesis method for 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b] pyridine-6-carboxylic acid

A technology of tert-butoxycarbonyl and octahydrofuran, which is applied in the field of synthesis of 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine-6-carboxylic acid, can solve the problem that is not suitable for industrial synthesis Methods and other issues, to achieve the effect of convenient operation, easy reaction, and short route

Active Publication Date: 2016-03-23
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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  • Synthesis method for 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b] pyridine-6-carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1: compound 1 (7.11g, 51.1mmol) was dissolved in ethanol (300mL), and thionyl chloride (36mL) 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 solution of sodium carbonate to make pH=7 to obtain the compound 2 used directly in the next step.

[0012] compound 2 Add water (150mL) to the solution, add sodium carbonate (7.33g, 0.307mol) and iodine (9.65g, 0.153mol), and react at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f =0.8) shows that the reaction is complete, and the reaction solution is added with 1N hydrochloric acid to make the pH=7 to precipitate a solid, which is filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (9.3g), yield 82%.

[0013] 1 CDCl 3 , δ1.36–1.40(m...

Embodiment 2

[0022] Embodiment 2: compound 1 (71.1g, 511mmol) was dissolved in ethanol (1500mL), and thionyl chloride (360mL) 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 solution of sodium carbonate to make pH=7 to obtain the compound 2 used directly in the next step.

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

[0024] 1 CDCl 3 , δ1.36–1.40(...

Embodiment 3

[0033] Embodiment 3: compound 1 (711g, 9.11mol) was dissolved in ethanol (5L), and thionyl chloride (3.6L) 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 solution of sodium carbonate to make pH=7 to obtain the compound 2 used directly in the next step.

[0034] compound 2 Add water (15L) to the solution, add sodium carbonate (733g, 30.7mol) and iodine (965g, 15.3mol), and react at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f =0.8) shows that the reaction is complete, and the reaction solution is added with 1N hydrochloric acid to make the pH=7 to precipitate a solid, which is filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (925g), yield 82.5%.

[0035] 1 CDCl 3 , δ1.36–1.40(m,3H)3.91(...

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Abstract

The present incention relates to a synthesis method for 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b] pyridine-6-carboxylic acid, and mainly solves the technical problem of no synthesis method suitable for industrialization at present. The synthesis method comprises six steps: first esterifying a compound 1 to obtain a compound 2; then performing iodination to produce a compound 3; acetylating the compound 3 to obtain a compound 4; then performing coupling to obtain a compound 5; performing cyclization to obtain a compound 6; performing hydrogenation to obtain a compound 7, then reacting with Boc anhydride to obtain a compound 8; and performing hydrogenation to obtain a final compound 9. The reaction formula is shown in the description.

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 Applications(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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