Method for preparing tetrahydropyran-3-potassium trifluoroborate

Abstract

The invention discloses a new method for preparing tetrahydropyran-3-potassium trifluoroborate. The method specifically comprises the following steps: preparing di-alpha-pinoborane by using dextro-alpha-pinene and a borane-dimethyl sulfide complex as raw materials, then reacting di-alpha-pinoborane with 3,4-dihydropyran at room temperature, then using anhydrous acetaldehyde for reduction to generate dimethyl borate, without separating an intermediate, and subsequently reacting dimethyl borate with a saturated aqueous solution of KHF2 to generate the target product tetrahydropyran-3-potassium trifluoroborate. The method has the obvious advantages that the reaction raw materials are easy to obtain; the reaction operation is simple; large-scale production is easy to achieve; the yield is high; the purity is good; the production cost is low.

Description

technical field [0001] The invention relates to a new method for synthesizing a pharmaceutical intermediate organic boric acid derivative, belonging to the field of organic chemical synthesis, in particular to a method for preparing potassium tetrahydropyran-3-trifluoroborate. Background technique [0002] Organoboronic acid and its derivatives are an important class of pharmaceutical intermediates and organic chemical reagents, which are widely used in organic synthesis to form new C-C single bonds through Suzuki-Miyaura coupling reactions. Most organic boronic acids are stable at room temperature and can be stored for a long time, but some alkyl boronic acids and alkene or alkyne boronic acids are unstable at room temperature and are prone to deterioration, so it is difficult to preserve this type of boronic acid. Certain difficulties, if this type of boric acid is converted into boric acid derivatives such as boric acid ester and potassium trifluoroborate, its properties ...

AI Technical Summary

Problems solved by technology

[0008] This method is based on tetrahydropyran and pinadate borate as raw materials, transition metal as catalyst and organic ligand, heating to 120°C in a sealed tube, and reacting for 12-14h to generate tetrahydropyran-3-boronic acid pina Alcohol esters and then with KHF 2 The reaction prepares tetrahydropyran-3-potassium trifluoroborate. Although the raw material tetrahydropyran and bisboronic acid pinadate are cheap in this method, the price of transition metal catalyst and organic ligand is quite expensive, and there are almost no The commercial product of the first raw material, the target product prepared is also a milligram-level product in the laboratory, and it is impossible to achieve scale-up production at all.

[0009] The above two known preparation methods all have the disadvantages of expensive raw materials, not easy to obtain, and harsh reaction conditions, and cannot realize scale-up production, which limits the mass production of the target product

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