Synthesis method of tert-butyl-8-oxo-2,6,9-triazaspiro[4.5]decane-2-formylate

A technology of a triazaspiro and a synthetic method, which is applied in the field of synthesis of tert-butyl-8-oxygenide-2,6,9-triazaspiro[4.5]decane-2-carboxylate, capable of Solve the problems of no suitable industrial synthesis method, etc., and achieve the effect of reasonable reaction process design, strong repeatability and simple route

Inactive Publication Date: 2019-03-22
上海合全医药有限公司
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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 tert-butyl-8-oxo-2,6,9-triazaspiro[4.5]decane-2-formylate
  • Synthesis method of tert-butyl-8-oxo-2,6,9-triazaspiro[4.5]decane-2-formylate

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Embodiment 1

[0013] Triethylamine (273.16 g, 2.70 mol, 375.74 mL) was added to a solution of compound 1 (250 g, 1.35 mol ) and ethyl glycine hydrochloride (207.24 g, 1.48 mol, HCl) in 1250 mL of methanol, Then titanium tetraisopropoxide (468.01 g, 1.65 mol, 485.99 mL) was added dropwise to the reaction solution at 20°C, and after the addition was completed, the mixed system was reacted at 25°C for 12 hours. Trimethylsilyl cyanide (149.98 g, 1.51 mol, 189.13 mL) was added to the reaction system at 25°C, and then reacted at 25°C for 12 hours, and the reaction solution was treated with water (1250 mL) and ethyl acetate (600 mL) and filtered, the filtrate was concentrated, ethyl acetate was added to stir and filtered, the organic phase was collected and concentrated under reduced pressure, the crude product was purified by column chromatography to obtain light yellow oily compound 2 (180 g) Yield: 45% . HNMR (400MHz, CHLOROFORM-d) δ= 3.71-3.77 (m, 4H), 3.46-3.58 (m, 5H), 2.28-2.33(s, 1H), 2.0...

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Abstract

The invention relates to a synthesis method of tert-butyl-8-oxo-2,6,9-triazaspiro[4.5]decane-2-formylate. The technical problem that an appropriate industrial synthesis method is inexistent at presentis mainly solved. The synthesis method is divided into two steps: the first step, adding triethylamine in a methanol solution dissolved with a compound 1 and amino ethyl acetate hydrochloride, and then dropwise adding tetraisopropyl titanate in the reaction solution, after completing the dropwise adding, reacting the mixed system for 12 h at 25 DEG C; adding trimethylsilyl cyanide in the reactionsystem at 25 DEG C, and then reacting for 12 h at 25 DEG C, performing post-treatment to obtain a compound 2; and the second step, adding the compound 2, nickel and ammonia water in the methanol solution, and performing hydrogenation to obtain the final compound.

Description

technical field [0001] The invention relates to a synthesis method of compound tert-butyl-8-oxygenide-2,6,9-triazaspiro[4.5]decane-2-carboxylate. Background technique [0002] The compound tert-butyl-8-oxyylidene-2,6,9-triazaspiro[4.5]decane-2-carboxylate (CAS: 1160247-09-5 ) and related derivatives in medicinal chemistry and Widely used in organic synthesis. 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 tert-butyl 8-oxygenidene-2,6,9-triazaspiro[4.5]decane- Synthesis of 2-formyl esters. It mainly solves the technical problem that there is no suitable industrial synthesis method at present. [0004] Technical scheme of the present invention: a kind of synthetic method of tert-butyl-8-oxyethylene-2,6,9-triazaspiro[4.5]dec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/10
CPCC07D487/10
Inventor 何米娜周强任文武李红李庆攀蒋欣欣吴东平何华敬安自强刘月领吴艳何燕平焦家盛于凌波马汝建
Owner 上海合全医药有限公司
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