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Synthesis method of 5-Boc-5-azaspiro [2.3] hexane-1-carboxylic acid

A 5-boc-5-, synthetic method technology, applied in the direction of organic chemistry, can solve the problems of troublesome separation, low yield, unstable intermediates, etc., and achieves the effect of improving yield and reducing cost

Pending Publication Date: 2022-02-25
GL BIOCHEM SHANGHAI +1
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Problems solved by technology

[0006] The purpose of this invention is to provide a kind of synthetic method of 5-Boc-5-azaspiro[2.3]hexane-1-carboxylic acid, which mainly solves the unstable intermediate, troublesome separation and low yield in the prior art. question

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  • Synthesis method of 5-Boc-5-azaspiro [2.3] hexane-1-carboxylic acid
  • Synthesis method of 5-Boc-5-azaspiro [2.3] hexane-1-carboxylic acid
  • Synthesis method of 5-Boc-5-azaspiro [2.3] hexane-1-carboxylic acid

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Embodiment 1

[0021] step 1:

[0022] Add tetrahydrofuran (1500 mL) to a 5-liter three-neck flask; add sodium hydrogen (70 g, 1.75 mol) at 0°C; dropwise add tert-butyl diethylphosphonoacetate (390 g, 1.546 mol) + tetrahydrofuran (500 mL )The solution. After the addition was completed and stirred at 0°C for 0.5 hours, a solution of 1-BOC-3-azetidinone (220 g, 1.286 mol) + tetrahydrofuran (500 mL) was added dropwise to the reaction solution, and the system was naturally stirred at room temperature for 3.5 Hours, the system clarifies.

[0023] The reaction system was poured into ice water, extracted with ethyl acetate (500 mL*2), the organic phase was separated, washed with saturated brine (300 ml), dried over anhydrous sodium sulfate, and the filtrate was spin-dried to obtain a colorless oily liquid, target Compound 1 (420 g, 1.56 mol, 121%).

[0024] Step 2:

[0025] Dimethyl sulfoxide (2000 mL) was added to a 5 L three-necked flask, sodium hydrogen (95 g, 2.375 mol) was added at 10°C, t...

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Abstract

The invention relates to a synthesis method of 5-Boc-5-azaspiro [2.3] hexane-1-carboxylic acid, and mainly solves the technical problems of unstable intermediate, troublesome separation, low yield and the like in the existing synthesis method. The synthesis method comprises the following steps of: reacting tert-butyl diethyl phosphonoacetate with sodium hydrogen in a tetrahydrofuran solution, and then adding 1-BOC-3-azetidinone to generate a compound 1; reacting the compound 1 with trimethyl sulfoxide iodide in a dimethyl sulfoxide solution under the action of sodium hydrogen to generate a compound 2; reacting the compound 2 with trifluoroacetic acid in a dichloromethane solution to generate a compound 3; and reacting the compound 3 with Boc2O in a dioxane aqueous solution to generate a target compound 4.

Description

technical field [0001] The present invention relates to a synthesis method of 5-Boc-5-azaspiro[2.3]hexane-1-carboxylic acid (cas: 1251012-82-4). Background technique [0002] The azaspiro ring structure is a kind of important mother nucleus in the natural structure, which widely exists in the alkaloids in nature. This kind of spiro ring compound often has important physiological activity and medicinal value due to its unique structure and properties. For example, cephalotaxine, cephalotaxine, is isolated from Torreya cylindrica and cloverwood, and is the precursor of anticancer drugs harringtonine and homoharringtonine; the marine natural product cylindricine A is isolated from sea squirt Clvaelina cylindrica The resulting tricyclic alkaloids. [0003] The prior art is the synthesis method of the compound disclosed in European Journal of Organic Chemistry 2021, and the reaction formula is as follows: [0004] [0005] The technical defect of this synthesis method is: th...

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Application Information

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IPC IPC(8): C07D205/12
CPCC07D205/12
Inventor 徐红岩戴健秦丽星周志国窦肖俊
Owner GL BIOCHEM SHANGHAI
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