6-tert-butyloxycarbonyl octahydro-2H-pyran[3,2-c]pyridine-8-carboxylic acid synthesis method

A technology for the synthesis of tert-butoxycarbonyl octahydro-2H-pyrano[3,2-c]pyridine-8-carboxylic acid, which can solve the problem of unsuitable Solve the problems of industrial synthesis methods and achieve the effects of convenient operation, easy reaction and short route

Active Publication Date: 2016-05-25
SHANGHAI STA PHARMA R&D CO LTD +1
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  • 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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  • 6-tert-butyloxycarbonyl octahydro-2H-pyran[3,2-c]pyridine-8-carboxylic acid synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: Dissolve compound 1 (8.0g, 0.0295mol) in tetrahydrofuran (60mL), cool to -20 degrees Celsius, add potassium tert-butoxide (8.8g, 0.0738mol), stir for half an hour, then dropwise add 1-Bromo-3-chloro-propane (7.0 g, 0.0443 mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio = 5: 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (30 mL), and extracted with ethyl acetate (20 mLx3). The organic phase was dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography. The eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20:1). After removing the solvent, compound 2 in yellow oil was obtained. (10.3 g), yield 100%.

[0011] Compound 2 (10.3g, 0.0295mol) was dissolved in tetrahydrofuran (80mL), sodium hydrogen (1.77g, 0.0441mol) was added under nitrogen p...

Embodiment 2

[0015] Example 2: Dissolve compound 1 (80g, 0.295mol) in tetrahydrofuran (600mL), cool to -20 degrees Celsius, add potassium tert-butoxide (88g, 0.738mol), stir for half an hour, then add dropwise 1- Bromo-3-chloro-propane (70 g, 0.443 mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio = 5: 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (300mL), and extracted with ethyl acetate (200mLx3). The organic phase was dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography. The eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20:1). After removing the solvent, compound 2 in yellow oil was obtained. (103 g), yield 100%.

[0016] Compound 2 (103g, 0.295mol) was dissolved in tetrahydrofuran (800mL), sodium hydrogen (17.7g, 0.441mol) was added under nitrogen protecti...

Embodiment 3

[0020] Example 3: Dissolve compound 1 (400g, 1.475mol) in tetrahydrofuran (4.0L), cool to -20 degrees Celsius, add potassium tert-butoxide (440g, 3.69mol), stir for half an hour, then dropwise add 1 -Bromo-3-chloro-propane (350 g, 2.215 mol), after the addition was complete, the reaction was warmed to 15°C overnight. TLC (petroleum ether: ethyl acetate volume ratio = 5: 1, R f =0.5) showed that the reaction was complete, the reaction mixture was quenched with saturated ammonium chloride solution (1.0L), and extracted with ethyl acetate (1.0Lx3). The organic phase was dried with anhydrous sodium sulfate and then concentrated. The residue was purified by column chromatography. The eluent ratio was (petroleum ether: ethyl acetate volume ratio = 20:1). Compound 2 in yellow oil was obtained after removing the solvent. (515 g), yield 100%.

[0021] Compound 2 (515g, 1.475mol) was dissolved in tetrahydrofuran (4.0L), sodium hydrogen (70g, 1.77mol) was added under nitrogen protectio...

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Abstract

The present invention relates to a 6-tert-butyloxycarbonyl octahydro-2H-pyran[3,2-c]pyridine-8-carboxylic acid synthesis method. In the prior art, the suitable industrial synthesis method does not exist. A purpose of the present invention is to mainly solve the technical problem in the prior art. The synthesis method comprises six steps and specifically comprises that a compound 1 and 1-bromo-3-chloro-propane are subjected to an alkylation reaction to obtain a compound 2, an intramolecular cyclization reaction is performed to generate a compound 3, the double bond of the compound 3 is subjected to hydrogenation reduction to obtain a compound 4, and the compound 4 is subjected to hydrolysis to obtain a compound. The reaction formula is defined in the specification.

Description

technical field [0001] A method for synthesizing the compound 6-tert-butoxycarbonyl octahydro-2H-pyrano[3,2-c]pyridine-8-carboxylic acid involved in the present invention. Background technique [0002] Compound 6-tert-butoxycarbonyloctahydro-2H-pyrano[3,2-c]pyridine-8-carboxylic acid (CAS: 1314378-07-8) and related derivatives have important roles in medicinal chemistry and organic synthesis widely used. Currently, the synthesis of 6-tert-butoxycarbonyl octahydro-2H-pyrano[3,2-c]pyridine-8-carboxylic acid is difficult. Therefore, it is necessary to develop a synthetic method with readily available raw materials, convenient operation, easy control of the reaction, and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a 6-tert-butoxycarbonyl octahydro-2H-pyrano[3,2-c]pyridine-8- Synthesis of carboxylic acids. It mainly solves the technical problem that there is no suitable industrial synthesis method at present....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
Inventor 任文武陈雅婷张金宝孟庆洪邱继平刘洋邢少廷于涵赵东王庆伟孙宝龙宁振翠靳爱杰卫凯龙要加军袁晓斌于凌波何振民马汝建陈民章傅小勇王文贵
Owner SHANGHAI STA PHARMA R&D CO LTD
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