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Synthesis method of racemic-(3aR,7aR)-5-(t-butyloxycarboryl)-octahydro furan [3,2-c] pyridine-3a- carboxylic acid

A technology of tert-butoxycarbonyl and octahydrofuran, applied in the synthesis field of racemic-5-(tert-butoxycarbonyl)-octahydrofuro[3,2-c]pyridine-3a-carboxylic acid, can solve the problem of There are no problems such as being suitable for industrial synthesis methods, and the effects of reasonable reaction process design, short route and convenient reaction operation are achieved.

Inactive Publication Date: 2017-11-24
上海药明康德新药开发有限公司 +4
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  • Application Information

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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 of racemic-(3aR,7aR)-5-(t-butyloxycarboryl)-octahydro furan [3,2-c] pyridine-3a- carboxylic acid
  • Synthesis method of racemic-(3aR,7aR)-5-(t-butyloxycarboryl)-octahydro furan [3,2-c] pyridine-3a- carboxylic acid

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Embodiment 1

[0012] Step 1: Dissolve compound 1 (250 g, 2 mol) and NMM (232.5 g, 2.2 mol) in dichloromethane (1000 mL), then add ethyl propiolate (294 g, 3 mol) at 0°C, Then react at room temperature for 3 hours, TLC (petroleum ether / ethyl acetate volume ratio=5 / 1) showed that the reaction was complete. The reaction solution was poured into water, and then the organic phase was separated, and the aqueous phase was extracted twice with dichloromethane, then dried and concentrated to obtain a crude product, which was subjected to column chromatography to obtain compound 2. Yield: 72%.

[0013] Step 2: Dissolve mixture 2 (200 g, 0.897 mol) and potassium carbonate (371.3 g, 2.69 mol) in dimethylformamide (1.0 L), and slowly add ethyl cyanoacetate dropwise at 0°C. Then react overnight at room temperature. TLC (petroleum ether / ethyl acetate volume ratio = 5 / 1) showed that the reaction was complete. Then the system was filtered, and the mother liquor was concentrated under reduced pressure. T...

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Abstract

The invention relates to a synthesis method of racemic-(3aR,7aR)-5-(t-butyloxycarboryl)-octahydro furan [3,2-c] pyridine-3a-carboxylic acid. The method mainly solves the technical problem that no proper industrial synthesis method exists in the prior art. The method comprises seven steps that: firstly, 2-bromoethanol and ethyl propiolate react in a solvent of methylene dichloride at the room temperature to obtain a compound 2; then, the compound 2 and ethyl cyanoacetate react in a solvent of N, N-dimethyl formamide at the room temperature over the night to obtain a compound 3; the compound 3 is subjected to catalytic hydrogenation to reduce the cyano groups to obtain amino groups; meanwhile, the exchange with the self ester is performed to obtain a compound 4; a compound 5 is obtained through carbobenzoxy chloride on the compound 4; the compound 5 is reduced by borane to obtain a compound 6; finally, the compound 6 uses a palladium hydroxide as a catalyst in ethanol; meanwhile, Boc estolide is added; hydrogen gas is introduced for overnight reaction to obtain a target compound 7; the compound 7 is hydrolyzed by water and lithium hydroxide in a mixed solution of methanol and water; a final target compound 8 is obtained.

Description

technical field [0001] The present invention relates to the synthesis method of the compound racemic-5-(tert-butoxycarbonyl)-octahydrofuro[3,2-c]pyridine-3a-carboxylic acid, that is, racemic-(3aR,7aR)-5 -Synthetic method of (tert-butoxycarbonyl)-octahydrofuro[3,2-c]pyridine-3a-carboxylic acid. Background technique [0002] Compound (3aR,7aR)-5-(tert-butoxycarbonyl)-octahydrofuro[3,2-c]pyridine-3a-carboxylic acid (CAS: 1314391-33-7) and related derivatives in Medicinal Chemistry It has wide applications in organic synthesis. Currently, there are few reports on the synthesis of rac-(3aR,7aR)-5-(tert-butoxycarbonyl)-octahydrofuro[3,2-c]pyridine-3a-carboxylic acid. 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 th...

Claims

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Application Information

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IPC IPC(8): C07D491/048
CPCC07D491/048C07B2200/07
Inventor 张大为周强赵红双高明飞于智宇姚宝元卢荣昌白有银孙春刘雨雷韩华欣付新雨卢仔倚李旭东于凌波马汝建
Owner 上海药明康德新药开发有限公司
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