51072-35-6Relevant academic research and scientific papers
Racemization recovery method of dextromethorphan hydrobromide intermediate byproducts
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Paragraph 0016; 0018; 0022, (2021/01/25)
A racemization recovery method of dextromethorphan hydrobromide intermediate byproducts comprises the following steps: 1) performing mother liquor treatment: under a stirring condition, carrying out reduced pressure distillation until methanol is basically evaporated completely, when the temperature of the concentrated mother liquor is lower than 40 DEG C, adding a sodium hydroxide solution, stirring, standing, detecting that the pH value is greater than 12, layering, recovering mandelic acid by using the obtained water phase, concentrating the obtained oil phase under reduced pressure until toluene is completely evaporated, and cooling to 65-80 DEG C; 2) performing N-chlorination: adding isopropanol, and dropwise adding a sodium hypochlorite solution; 3) performing racemization: adding liquid caustic soda into the reaction system, and stirring for reaction; 4) reducing: dropwise adding a sodium borohydride solution, and reacting completely; 5) performing chiral resolution: adding methanol and D-mandelic acid into the toluene solution of a compound (I), and carrying out chiral resolution; and (6) refining the mother liquor: treating the mother liquor obtained in step (5) as a raw material according to the treatment methods in steps (1)-(4) to obtain a mother liquor prepared compound (I) methylbenzene solution, and adding oxalic acid for refining.
By using micro-reactor racemic recovery dextromethorphan chiral intermediate split by-product of the method (by machine translation)
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Paragraph 0019-0023, (2019/11/14)
The invention discloses a method which utilizes a micro reactor racemic recovery dextromethorphan chiral intermediate split by-product of the method, characterized in that in a microchannel reactor, R - 1 - (4 - methoxybenzyl) - 1, 2, 3, 4, 5, 6, 7, 8 - eight hydrogens different quinoline solution and hypohalous acid salt solution two material continuously into the reactor, micro-reactor outlet mixture through continuous tank reactor in alkali under the effect of the elimination reaction, the reactant by extraction after treatment and reduction to obtain 1 - (4 - methoxybenzyl) - 1, 2, 3, 4, 5, 6, 7, 8 - eight hydrogens different quinoline racemate. The invention reaction time is short, the operation is safe, high yield, the arylation compound impurity 1 - (4 - methoxybenzyl) - 5, 6, 7, 8 - tetrahydroisoquinoline of impurities less, wastes less, is suitable for industrial production. (by machine translation)
Method for preparing levallorphan tartrate
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, (2017/08/29)
The invention provides a method for preparing levallorphan tartrate and belongs to the technical field of drug and chemical synthesis. The method takes methoxyphenylacetic acid and 2-(cyclohexenyl)ethylamine as initial raw materials, and comprises nine reaction steps such as acylation condensation, Bischler-Napieralski ring formation reaction, imine reduction, ether bond hydrolysis, resolution, N-alkylation, Grewe cyclization reaction, and salifying. According to the method, the levallorphan tartrate and each intermediate can be obtained at high yield and high purity, and the method can serve as an industrial method for performing large-scale production.
A process for preparing dextromethorphan method
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, (2018/02/04)
The invention relates to a novel method for preparing dextromethorphan. When the method is used for preparing an intermediate (+)-1-(4-methoxy) benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline (VI), a catalytic reducing method is adopted to carry out chiral reduction on 1-(4-methoxy) benzyl-3,4,5,6,7,8-hexahydroisoquinoline (VI), so that the intermediate is prepared with high selectivity. The novel method disclosed by the invention can cancel complex operations such as chiral resolution, is simple to operate, gentle in reaction condition, short in total time, wide in material source, and very suitable for industrially producing dextromethorphan.
Racemization recycling method for byproduct in resolution mother liquor of dextromethorphan hydrobromide midbody
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Paragraph 0047; 0048, (2017/01/17)
The invention relates to a racemization recycling method for a resolution byproduct in a dextromethorphan hydrobromide midbody 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline. The racemization recycling method is characterized by comprising the following steps: (1) resolving racemic 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline by using D-mandelic acid or D-tartaric acid so as to obtain D-mandelic acid or D-tartrate and 1,2,3,4,5,6,7,8-octahydro-R-1-[(4-methoxy phenyl) methyl] isoquinoline of a 1,2,3,4,5,6,7,8-octahydro-S-1-[(4-methoxy phenyl) methyl] isoquinoline compound; (2) oxidizing the 1,2,3,4,5,6,7,8-octahydro-R-1-[(4-methoxy phenyl) methyl] isoquinoline so as to obtain 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline; (3) reducing the 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline, thereby obtaining the dextromethorphan midbody 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline. The racemization recycling method for the byproduct, namely, a levogyration midbody of dextromethorphan, is gentle in condition, simple and convenient to operate and small in material consumption.
AlCl3·6H2O/KI/H2O/CH3CN: A new alternate system for dehydration of oximes and amides in hydrated media
Boruah, Monalisa,Konwar, Dilip
, p. 7138 - 7139 (2007/10/03)
Dehydration of oximes and amides to nitriles was carried out using the AlCl3·6H2O/KI/H2O/CH3CN system. It produced isoquinoline derivatives 8a-c (Bischler Naperialski reaction) when reacted with amides 7a-c in hydrated media. Also, the keto oximes produced anilides (Beckmann rearrangement) with the system under the same reaction conditions.
Aluminium chloride and sodium iodide (AlCl3-Nal): A versatile dehydrating agentt
Konwar, Dilip,Boruah, Monalisa,Sarmah, Gautom Kumar,Bhattacharyya, Nayan Kamal,Borthakur, Naleen,Goswami, Birendra Nath,Boruah, Kumar Ranjan
, p. 490 - 492 (2007/10/03)
AlCl3-Nal is an efficient reagent for dehydration of oximes, amides and the Beckmann rearrangement of ketoximes to anilides; it forms isoquinoline derivatives 8(a-c) by cyclodehydrating amides 7(a-c) in very good yields at room temperature.
Process for manufacture of optically active isochinole compounds
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, (2008/06/13)
A process for the manufacture of optically active (R)- or (S)-1-(4-methoxy-benzyl)-1,2,3,4,5,6,7,8-octahydro-isoquinoline adducts of the formula STR1 wherein HX signifies a mineral acid from the group of HBF4, H2 SO4, HPF6, HBr, HI, HCl, HSbF6 or HClO4, or a strong organic acid from the group of C1-8 -alkylSO3 H, picric acid, formic acid, a lower alkylsulphonic acid or arylcarboxylic acid or a dicarboxylic acid, from a compound of the formula STR2 wherein HX has the significance given above, by asymmetric hydrogenation in the presence of a complex consisting of optically active diphosphine ligands with iridium, optionally in the presence of an additive.
Process for preparing optically active 1-(p-methoxybenzyl)-1,2,3,4,5,3,7,8-octahydroisoquinoline
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, (2008/06/13)
Optically active 1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline having the formula (I) is prepared by asymmetric hydrogenation of the corresponding 3,4,5,6,7,8-hexahydro-compound or of the new 1-(p-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinoline dihydrogenated phosphate in the present of chiral iridium-phosphine complexes. This product is an intermediate product in the synthesis of cough-relieving dextromethorphanne and analgesic levorphanol. STR1
GENERAL ASYMMETRIC SYNTHESIS OF BENZOMORPHANS AND MORPHINANS VIA ENANTIOSELECTIVE HYDROGENATION
Kitamura, M.,Hsiao, Yi,Noyori, R.,Takaya, H.
, p. 4829 - 4832 (2007/10/02)
A variety of optically active benzomorphans including metazocine and pentazocine as well as dextromethorphan, a morphinan, are obtainable by using the BINAP-ruthenium(II) catalyzed enantioselective hydrogenation as key operation.
