30356-08-2Relevant articles and documents
Racemization recovery method of dextromethorphan hydrobromide intermediate byproducts
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, (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.
Method for preparing (S)-1-(4-methoxy benzyl)-1, 2, 3, 4, 5, 6, 7, 8-octahydro isoquinoline
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Paragraph 0009; 0013; 0015; 0017, (2018/09/08)
The invention discloses a method for preparing (S)-1-(4-methoxy benzyl)-1, 2, 3, 4, 5, 6, 7, 8-octahydro isoquinoline which is a dextromethorphan intermediate. The method includes selectively hydrogenating 1-(4-methoxy benzyl)-3, 4, 5, 6, 7, 8-octahydro isoquinoline (II) under the condition of (R)-N-(5-fluorine-2-hydroxyl benzyl)-2-methylpropane-2-sulfinamide and trichlorosilane to obtain the (S)-1-(4-methoxy benzyl)-1, 2, 3, 4, 5, 6, 7, 8-octahydro isoquinoline (I). The 1-(4-methoxy benzyl)-3, 4, 5, 6, 7, 8-octahydro isoquinoline (II) is used as a raw material, and the (R)-N-(5-fluorine-2-hydroxyl benzyl)-2-methylpropane-2-sulfinamide is used as an organic chiral ligand. The method has the advantages that the organic chiral ligand is used, and the raw material is inexpensive, safe, simpleand easily available; the reaction temperatures range from -20 DEG C to -15 DEG C, and accordingly the method can be implemented in industrial production; an ee (enantiomeric excess) value of the (S)-1-(4-methoxy benzyl)-1, 2, 3, 4, 5, 6, 7, 8-octahydro isoquinoline which is a product can reach 63%.
A process for preparing dextromethorphan method
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Paragraph 0177; 0182; 0183, (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.