Method for synthesizing 3-(Boc-aminomethyl)cyclobutanone

A technology of aminomethylcyclobutanone and 3-boc-, which is applied in the field of synthesis of 3-Boc-aminomethylcyclobutanone, can solve the problems of troublesome post-processing and high cost of raw materials, and achieve simple post-processing and low reagent cost Low, high yield effect

Active Publication Date: 2018-12-21
GL BIOCHEM SHANGHAI
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Problems solved by technology

[0005] The purpose of the present invention is to provide a synthetic method of 3-Boc-aminomethylcyclobutanone, which ma

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  • Method for synthesizing 3-(Boc-aminomethyl)cyclobutanone

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Embodiment 1

[0011] step 1:

[0012] Add 3-oxocyclobutane carboxylic acid (45.0 g, 395 mmol) and methanol (250 mL) into a 500 ml three-necked flask; add trimethyl orthoformate (75 ml, 713 mmol) at room temperature; p-toluenesulfonic acid Monohydrate (2.0 g, 10.5 mmol). After heating and reflux stirring for 5 hours after the addition, the reaction solution was cooled to room temperature, most of the methanol was spun off, a saturated sodium bicarbonate solution (500 mL) was added, ethyl acetate (300 mL*2) was added for extraction, the organic phase was separated, and water (300 mL) and saturated brine (300 ml), and dried over anhydrous sodium sulfate. The filtrate was spin-dried to obtain a colorless oily liquid, the target compound 1 (71.5 g, 411 mmol, 104%). 1 H NMR (400 MHz, CDCl 3 ):3.71 (s, 3H), 3.17 (d, J=8.2 Hz, 6H), 2.90(p, J=8.7 Hz, 1H), 2.49-2. 36 (m, 4H).

[0013] Step 2:

[0014] Add compound 1 (60.0 g, 344 mmol) and methanol (500 mL) into a 1000 ml three-neck flask; add be...

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Abstract

The invention relates to a method for synthesizing 3-(Boc-aminomethyl)cyclobutanone. The method for synthesizing 3-(Boc-aminomethyl)cyclobutanone provided by the invention mainly solves the technicalproblems of high raw material cost and relatively difficult post-processing according to the existing synthesis method. The method for synthesizing 3-(Boc-aminomethyl)cyclobutanone provided by the invention comprises the following steps: 3-oxocyclobutanecarboxylic acid and trimethyl orthoformate are reacted in the methanol solution to generate a compound 1; the compound 1 and benzylamine are reacted in the methanol solution under an action of sodium methoxide to generate a compound 2; the compound 2 and sodium bis(2-methoxyethoxy)aluminiumhydride are reacted in tetrahydrofuran solution to generate a compound 3; the compound 3 is subjected to a Pd/C debenzylation and hydrogenation operation in the methanol solution to obtain a compound 4; the compound 4 and Boc2O are reacted in the methanolsolution to obtain a compound 5; the compound 5 is reacted in a 0.05 M hydrochloric acid solution generate a target compound 6. By performing an enzymatic catalyzed deglandulation action of on the corresponding prochiral 3-substituted cyclobutanone, a series of gamma-butyrolactone derivatives, including some spiro derivatives, can be obtained; and all the derivatives are inhibitors having good biological activity.

Description

technical field [0001] The present invention relates to the synthesis of 3-Boc-aminomethylcyclobutanone (CAS: 130369-09-4). Background technique [0002] Four-membered ring compounds Highly reactive four-membered ring products include cyclobutane, oxetane, azetidine, etc. This kind of compound can be functionalized at various positions on the ring, and can be used to design and synthesize a series of biologically active compounds, and has a wide range of applications. For example, L-azetidine-2-carboxylic acid (2133-34-8) is an anti-angiogenesis inhibitor by inhibiting collagen synthesis. A series of γ-butyrolactone derivatives, including some spiro derivatives, were obtained by enzyme-catalyzed deadenation of the corresponding prochiral 3-substituted cyclobutanones, all of which have good biological activities inhibitors. [0003] traditional method [0004] . Contents of the invention [0005] The purpose of the present invention is to provide a synthetic method o...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C271/18
CPCC07C67/08C07C213/02C07C231/02C07C269/04C07C269/06C07C2601/04C07C271/18C07C271/16C07C217/52C07C235/40C07C69/757
Inventor 徐红岩崇东升王杰郑莉莉
Owner GL BIOCHEM SHANGHAI
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