45 results about "Borane dimethylsulfide" patented technology

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (2-fluorin- 6-(trifluoromethyl) pyridine-3-yl) methanol. According to the invention, a compound A is used as an initial raw material and reacts with diisopropylamine under the catalysis of n-butyllithium to obtain a compound B, and the compound B reacts with borane dimethyl sulfide to obtain the (2-fluorine-6-(trifluoromethyl) pyridine-3-yl) methanol, so that the synthesis method of the (2-fluorine-6 (trifluoromethyl) pyridine-3-yl) methanol is provided for the first time. The synthetic method provides a synthetic route for the synthesis of the (2-fluorine-6 (trifluoromethyl) pyridine-3-yl) methanol, and is short in route, reasonable in design, simple to operate and easyto control.

The invention discloses a synthesis method of S-beta-hydroxy-gamma-butyrolactone, comprising the steps of: synthesis of L-dimethyl ester malate, synthesis of 3, 4-dihydroxybutyric acid methyl ester, synthesis of S-hydroxy-gamma-butyrolactone and the like.The synthesis method mainly adopts BiBr3/ hydroborate/ lower alcohol reducing system to selectively reduce monoester into alcohol, so that borane dimethyl sulfide composite which is combustible and explosive, is not easily stored and has high price in the prior art is avoided being used. The synthesis method of the S-beta-hydroxy-gamma-butyrolactone is suitable for industrialized production.

A preparing method of (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine that is a lorcaserin intermediate is disclosed. The method includes (1) dehydrating a compound 1 and a compound 2 under catalysis by boric acid to generate an amide 3, (2) reducing the intermediate 3 with a borane dimethylsulfide complex to obtain a compound 4, and (3) subjecting the compound 4 to direct ring closing with the existence of aluminum chloride to generate the lorcaserin intermediate that is the (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine that is the compound 6. The method avoids use of 3,4,5-trimethoxyphenylboronic acid that is an expensive reagent, thus reducing the cost. The method avoids use of thionyl chloride so that the method is environmental friendly. A step of hydroxy chlorination is reduced so that the method is simple in process. The conversion ratio of raw materials and the total yield of reactions are increased. The yield of the compound 6 is increased from 60% in a patent to 82%. The method is suitable for industrial production. A reaction equation is shown in the description.

The invention relates to a preparation method of chiral S/R-3-ethoxy-4-methoxy-alpha[(methylsulfonyl)methyl] benzyl alcohol. The preparation method comprises the following steps: 3-hydroxy-4-methoxybenzaldehyde is taken as a starting material and reacts with hydroxylammonium hydrochloride to produce 3-hydroxy-4-methoxybenzonitrile; 3-hydroxy-4-methoxybenzonitrile reacts with bromoethane to produce 3-ethoxy-4-methoxybenzonitrile; 3-ethoxy-4-methoxybenzonitrile reacts with dimethyl sulfone under the action of n-butyllithium, a product is hydrolyzed in an aqueous hydrochloric acid solution, and 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanone is obtained; finally, S-(-)-alpha,alpha-diphenyl-2-pyrrolidinemethanol or R-(+)-alpha,alpha-diphenyl-2-pyrrolidinemethanol is taken as a chiral catalyst, a borane dimethyl sulfide solution is taken as a reducing agent, carbonyl is reduced, and a product is obtained. The reaction conditions are mild, the product yield is higher, the technology level is increased, the operability is improved, and large-scale industrial production is facilitated.

The invention relates to a preparation method of a sitafloxacin side chain intermediate. The preparation method comprises the following steps: synthesizing 4-methyl acetoacetate with 1,2-dibromoethane into a three-membered ring, synthesizing the three-membered ring with ammonia water into nitrogen heterocycle, synthesizing nitrogen heterocycle with R-1-phenyl ethylamine to generate chiral carbon, reducing through sodium borohydride, adding ditertbutyl dicarbonate to generate a protecting group, and finally performing carbonyl reduction to borane-dimethyl sulfide to obtain an intermediate. According to the preparation method, the atom utilization rate can be improved, the use of toxic reagents can be reduced, and the amplification of the technology can be facilitated.

The invention discloses a liquid hydrocarbon fuel low-temperature self-ignition adjusting method based on an atomic carrier, and relates to the field of aviation fuels. Through the atom carrier additive, the combustion energy barrier of a substrate fuel is reduced, and low-temperature self-ignition of the hydrocarbon fuel is realized; the atomic carrier additive is a borane dimethyl sulfide complex; the substrate fuel is mixed fuel of octene, hexene or olefin and RP-3 kerosene. The method has the advantages of real-time ignition regulation and control, low self-ignition temperature, high safety and the like, the low-temperature spontaneous combustion characteristic of the liquid hydrocarbon fuel can be efficiently regulated and controlled, and the method is easy to operate and high in practicability.

The invention relates to a light-sensitive Zr-B-Si-C ceramic precursor and an in-situ preparation method thereof. The method comprises the following steps: uniformly mixing methylvinyldichlorosilane and a borane dimethyl sulfide complex, and then adding metal sodium for dechlorination to obtain methylvinyl borosilane; uniformly mixing chloromethyltrichlorosilane, methylchloromethyldichlorosilane and bis(cyclopentadienyl)zirconium dichloride, then adding metal magnesium to carry out a first heat preservation reaction, and then adding a reducing agent to carry out a second heat preservation reaction to obtain polyzirconocarbosilane; uniformly mixing methylvinyl borosilane and polyzirconocarbosilane to obtain vinyl Zr-B-Si-C alkane; and uniformly mixing the vinyl Zr-B-Si-C alkane with mercaptopropionate, and then adding a photoinitiator to initiate a polymerization reaction to prepare the ceramic precursor. The problems of high viscosity, high thermal stress, structural member mechanicalproperty attenuation and the like of a traditional photocuring system are solved, and a high-quality raw material is provided for photocuring 3D printing of an ultrahigh-temperature ceramic structuralmember.

The invention discloses a method for preparing a medical intermediate (E)-3-ethyl acrylate pinaborate. 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 ethyl propiolate at room temperature, then using anhydrous acetaldehyde for reduction to generate dimethyl borate and then reacting dimethyl borate with pinacol to generate (E)-3-ethyl acrylate pinaborate. 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.

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.

The invention discloses a method for preparing tetrahydrofuran-3-boric acid pinacol ester. The method comprises the following steps: preparing bi-alpha-isopoinocamphenylborane by using dextro-alpha-pinene and borane-methyl sulfide complex as raw materials; then performing reaction on bi-alpha-isopoinocamphenylborane and 2,5-dihydrofuran at a room temperature; performing reduction by using anhydrous acetaldehyde to produce bimethyl borate without needing separation of a midbody; subsequently, performing reaction on bimethyl borate and pinacol to produce a tetrahydrofuran-3-boric acid pinacol ester target product. The method has the obvious advantages of easily-available reaction raw materials, simple reaction operation, easiness for realization of large-scale production, high yield, high purity and low production cost.

The present invention discloses a synthesis process for 2-(2-bromoethyl)benzoic acid methyl ester. According to the synthesis process, easily-available 2-formyl benzoic acid methylester is adopted as a raw material, and reacts with methyl triphenylphosphine hydroiodide in the presence of a strong base to obtain 2-methyl vinylbenzoate; the 2-methyl vinylbenzoate reacts with a borane dimethyl sulfide complex; 2-(2-hydroxyethyl)benzoic acid methyl ester is produced under conditions of sodium hydroxide and hydrogen peroxide; and finally the 2-(2-hydroxyethyl)benzoic acid methyl ester is converted into the 2-(2-bromoethyl)benzoic acid methyl ester under conditions of triphenylphosphine and carbon tetrabromide.

The present invention relates to a method for synthesizing an anacetrapib intermediate (1R,2S)-1-(3,5-bis(trifluoromethyl)phenyl)-2-Boc-amino-propanol. The method comprises: adding (R)-2-methyl-CBS-oxazaborolidine and a borane-dimethyl sulfide complex to 1-(3,5-bis(trifluoromethyl)phenyl)-2-Boc-amino-acetone in a certain solvent at a certain temperature, and carrying out a reducing reaction. According to the present invention, the chiral catalytic reaction does not use the expensive metallic ruthenium catalyst, the catalytic selectivity is high, the reaction condition is mild, the product is single, the obtained intermediate has the high optical purity and the high yield, the production cost is low, and the method is environment is environmentally friendly, and is suitable for Industrial production.

The invention discloses a synthesis method of Mirabegron. The synthesis method comprises the following processing steps of S1, under the room-temperature condition, adding R-2 (amino-N-methylbenzylamine) benzyl alcohol,2-(2-Aminothiazole-5-based)-N-[4-(2-Chloro-Ethyl)-Phenyl]-Acetamide and triethylamine to a solvent, and performing reflowing for 8h; S2, after the reaction is finished, pumping reaction liquid into water, and performing filtering to obtain the Mirabegron. In the step S1, the solvent is one or more of methanol, ethanol, propanol, dichloromethane, tri- chloromethane, acetone, butanone and toluene. An organic solvent which has stimulability is not used, a borane-methyl sulfide complex having high risk is not used, high temperature and high pressure are not adopted, the reactionprocess is green and environmental-friendly, clean production is realized, the cost is reduced, and the synthesis method has good market competitiveness.

The invention discloses a preparation method of 2,2,2-trifluoro-N-[(1S,4S)-4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl]-acetamide. The preparation method comprises the following steps: performing asymmetric reduction on 2,2,2-trifluoro-N-[(S)-4-carbonyl-1,2,3,4-tetrahydronaphthalene-1-yl]-acetamide under the action of chiral oxazaborolidine derivative and borane-methyl sulfide to obtain a 2,2,2-trifluoro-N-[(1S,4S)-4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl]-acetamide reaction solution; after the reaction ends, adding diluted hydrochloric acid for quenching, filtering, pulping with water, and carrying out solid drying to obtain a pure product, wherein the yield is 95.0% or higher, the purity is 99.0% or higher, and the ee% value is 99.0% or higher. According to the preparation method disclosed by the invention, the asymmetric reduction is carried out under the combined action of chiral oxazaborolidine derivative and borane-methyl sulfide, the reaction is simple in operation, the preparation period is shortened, the manufacturing cost is reduced, the generation of solid waste and solid water is greatly reduced, the preparation method is beneficial for environmental protection, and the investment of an enterprise for the disposal of waste is reduced.

The invention discloses a novel method for preparing tetrahydropyrane-3-boronic acid pinacol ester. The new method specifically comprises the following steps: taking a dextrorotation alpha pinene and dimethyl sulfide borane complex compound as raw materials, preparing di-alpha pinene borane, then reacting with 3,4-dihydropyran at a room temperature, reducing with anhydrous acetaldehyde to generate dimethyl borate, needing no intermediate separation and successively reacting with pinacol to generate a target product, namely the tetrahydropyrane-3-boronic acid pinacol ester. The method has the obvious advantages of high easiness in obtaining of reaction raw materials, high simplicity in reaction operation, high easiness in realization of mass production, high yield, good purity and low production cost.

The invention provides a method for reducing diyne compounds. The method for reducing the compounds represented by a formula I comprises the following steps: (1) a system of a borane reagent and tetrahydrofuran is provided, wherein the borane reagent is a borane dimethylsulfide solvent; (2) cyclohexene is dropped into the system of borane reagent and tetrahydrofuran, such that a borane system comprising active hydrogen is obtained; (3) the compound represented by the formula I is added into the borane system comprising active hydrogen, and a reduction reaction is carried out, such that a compound represented by a formula II can be obtained. With the method, diyne compounds can be effectively reduced into diene compounds. In the entire process of the method, reaction materials are easy to obtain; reaction post-treatment is simple; industrial three-waste treatment is easy; and target product yield is high. The method is suitable for industrialized productions.

The invention discloses a new method for preparing tetrahydrofuran-3-potassium trifluoroborate. The new 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 2,5-dihydrofuran 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 tetrahydrofuran-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.