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Stabilizer-containing borane reagent combination solution, and preparation method and use thereof

A technology of stabilizer and borane dimethyl sulfide complex, applied in the field of combined solutions, can solve problems such as non-obviousness, and achieve the effects of increasing stability, reducing waste and reducing costs

Active Publication Date: 2018-05-22
上海福乐医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the impact of adding stabilizers such as borohydride to the tetrahydrofuran solution of the borane dimethyl sulfide complex has not been reported. Therefore, the tetrahydrofuran of the borane dimethyl sulfide complex containing borohydride The stability of the solution and the reduction properties, e.g., the effect on the enantioselectivity of asymmetric reduction reactions, are not obvious

Method used

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  • Stabilizer-containing borane reagent combination solution, and preparation method and use thereof
  • Stabilizer-containing borane reagent combination solution, and preparation method and use thereof
  • Stabilizer-containing borane reagent combination solution, and preparation method and use thereof

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Embodiment 1

[0035] The preparation of embodiment 1 borane dimethyl sulfide complex (BDMS)

[0036] Purge the glass reaction flask with nitrogen and simultaneously charge 660 grams of dimethyl sulfide, lower the temperature in the reaction flask to 0°C, and bubble 138 grams of diborane into the reaction flask after 1 hour. During the process, the temperature was controlled at 0-5° C., and the stirring reaction was continued for 15 minutes after the introduction of diborane was completed. After detection, the density of the borane dimethyl sulfide complex obtained by the reaction is 0.80 g / mL, and the concentration of borane (ie, the borane dimethyl sulfide complex) is 10.08 mol / liter (M).

Embodiment 2

[0037] The preparation of embodiment 2 borane tetrahydrofuran complexes (BTHF)

[0038] The glass reaction flask was purged with nitrogen and 353.8 grams of tetrahydrofuran was charged at the same time, the temperature in the reaction flask was lowered to 0° C., and diborane (11.8 grams) was bubbled into the reaction flask for 0.5 hours. During the bubbling process, , control the temperature at 0-5° C., and continue stirring for 15 minutes after the diborane is passed through. After testing, the density of the solution after the reaction was 0.87 g / mL, and the concentration of borane (ie borane tetrahydrofuran complex) was 2 mol / L.

[0039] Add sodium borohydride to the borane tetrahydrofuran complex solution prepared above, so that the final concentration of sodium borohydride in the solution is 0.005M, that is, the molar ratio of sodium borohydride to borane tetrahydrofuran complex is 1:400 . After the addition of sodium borohydride was complete, the solution was stirred f...

Embodiment 3

[0040] Embodiment 3 Stabilizer type (sodium borohydride, potassium borohydride and lithium borohydride) is on the influence of the stability of the tetrahydrofuran solution of borane dimethyl sulfide complex and under the same conditions, the tetrahydrofuran of borane tetrahydrofuran complex Comparison of Stability of Solution and Tetrahydrofuran Solution of Borane Dimethyl Sulfide Complex

[0041] Using tetrahydrofuran as a solvent, dilute the borane dimethyl sulfide complex obtained in Example 1 to about 2 mol / liter, then divide the diluted solution into four equal parts, and add Sodium borohydride, potassium borohydride, lithium borohydride, so that the final concentration of the three stabilizers in the solution is 0.005M, that is, the molar ratio of borane dimethyl sulfide complex to sodium borohydride is 400:1. After adding sodium borohydride and lithium borohydride, the solution was stirred for 1 hour to dissolve the stabilizer to obtain solutions B and C; after adding ...

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Abstract

The invention provides a stabilizer-containing borane reagent combination solution. The borane reagent combination solution comprises a borane-dimethyl sulfide complex, tetrahydrofuran and a stabilizer, wherein the concentration of the borane-dimethyl sulfide complex in tetrahydrofuran is 1-10 mol / L, and a molar ratio of the borane-dimethyl sulfide complex to the stabilizer is 100:1 to 1000:1. Thecombination solution has the advantages of high concentration, good thermal stability, realization of high-efficiency utilization of a reaction container, and saving of the tetrahydrofuran reagent toreduce the cost; and the combination solution achieves a good reaction enantioselectivity and a high enantiomeric excess value (% ee) of a product when applied to Corey asymmetric reduction.

Description

technical field [0001] The invention relates to a combination solution, in particular to a stabilizer-containing borane reagent combination solution, its preparation method and application. Background technique [0002] Diborane (B 2 h 6 ) is a toxic, pyrophoric gas, very easy to hydrolyze and oxidize. It must be handled with extreme care and must be transported and stored at temperatures below -20°C. In order to reduce the risk of using diborane, borane (BH 3 ) for organic reactions of complexes with electron-donating molecules such as tetrahydrofuran, thioethers, amines, and phosphine, especially for functional group reduction and hydroboration reactions with alkenes and alkynes. Functional groups reduced by these borane complexes include aldehyde, ketone, lactone, epoxide, ester, amide, oxime, imine, and nitrile groups. [0003] The most common commercial source of borane is a solution of borane tetrahydrofuran complex (BTHF) in tetrahydrofuran (THF), which is commer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/02C07B53/00C07C29/143C07C33/46C07F5/02
CPCC07B41/02C07B53/00C07B2200/07C07C29/143C07F5/027C07C33/46
Inventor 张蕴仪雷新胜
Owner 上海福乐医药科技有限公司
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