30356-08-2

Basic information

• Product Name: (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8&
• Synonyms: (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8&;(R)-1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxyphenyl)methyl]isoquinoline;OCTABASE;Einecs 250-145-0
• CAS NO: 30356-08-2
• Molecular Formula: C₁₇H₂₃NO
• Molecular Weight: 257.37062
• EINECS: 250-145-0
• Product Categories: CMLLYL
• Mol File: 30356-08-2.mol

Chemical Properties

• Boiling Point: 394.8°Cat760mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.108 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.565(lit.)
• PKA: 10.20±0.40(Predicted)
• CAS DataBase Reference: (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8&(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8&(30356-08-2)
• EPA Substance Registry System: (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8&(30356-08-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 30356-08-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8& is used as a building block in the synthesis of various pharmaceutical compounds for its ability to modulate biological targets and receptors. This property makes it a valuable component in drug discovery and development, contributing to the creation of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8& is employed as a key component in the development of agrochemical products. Its role in modulating biological targets and receptors aids in the creation of effective pesticides, herbicides, and other agricultural chemicals.
Used in Organic Synthesis:
(R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8& is utilized as a starting material in organic synthesis, enabling the production of a diverse range of compounds with various applications. Its versatility in chemical reactions makes it an essential component in the synthesis of specialty chemicals, fine chemicals, and other complex organic molecules.
Used in Chemical Industry:
(R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8& (R)-1-(4-METHOXYBENZYL)-1 2 3 4 5 6 7 8& is also used across the broader chemical industry for its potential applications in the synthesis of compounds with different uses. Its presence as a chiral building block allows for the development of enantiomerically pure compounds, which are crucial in various chemical processes and applications.

InChI:InChI=1/C17H23NO/c1-19-15-8-6-13(7-9-15)12-17-16-5-3-2-4-14(16)10-11-18-17/h6-9,17-18H,2-5,10-12H2,1H3/t17-/m1/s1

Upstream product

• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 94992-57-1 (R)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline L-mandelate 
• 93477-35-1 (+/-)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline hydrobromide 
• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 104-01-8 4-Methoxyphenylacetic acid 
• 74570-02-8 4-((R)-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 63477-91-8 2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline 

Downstream Products

• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 30356-07-1 (1S)-1-[(4-methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 67596-84-3 (+)-2-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline 

Relevant articles and documents

Racemization recovery method of dextromethorphan hydrobromide intermediate byproducts

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.

Imine Reductase-Catalyzed Enantioselective Reduction of Bulky α,β-Unsaturated Imines en Route to a Pharmaceutically Important Morphinan Skeleton

The morphinan skeleton is an important sub-structure in many medicines such as dextromethorphan, and can be constructed from 1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (1-benzyl-OHIQ) derivatives. 1-Benzyl-3,4,5,6,7,8-hexahydroisoquinolines (1-benzyl-HHIQs), the precursors of 1-benzyl-OHIQs, constitute a type of bulky α, β-unsaturated imines. Until now, the application of imine reductases (IREDs) to α, β-unsaturated imines has only rarely been reported. In this study, through evaluation of 48 IREDs, both enantiomers of 1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline (1-(4-methoxybenzyl)-OHIQ) were obtained in high yield and excellent optical purity. Among the enzymes, the most steric hindrance-tolerant IRED from Sandarearacinus amylolyticus (IR40) was able to convert various phenyl substituted 1-benzyl-HHIQ to the corresponding 1-benzyl-OHIQ derivatives with excellent enantiometric excess. These results provide an effective route to synthesize these important compounds via enantioselective reduction of bulky α, β-unsaturated imine precursors, which can be readily prepared from 2-(1-cyclohexenyl)ethylamine and corresponding aryl acetic acids. (Figure presented.).

Method for preparing (S)-1-(4-methoxy benzyl)-1, 2, 3, 4, 5, 6, 7, 8-octahydro isoquinoline

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 (S) or (R)- 1 - (4 - methoxybenzyl) - 1, 2, 3, 4, 5, 6, 7, 8 - quinoline of eight hydrogens different preparation method

The invention discloses a preparation method of (S) or (R)-1-(4-methoxy benzyl)-1,2,3,4,5,6,7,8-octahydro isoquinoline acetate, wherein the method includes the steps: (1) mixing an aromatic solution of a compound having a structure represented by the formula III with acetic acid, to obtain a solution 1; (2) adding a (S)-1-(4-methoxy benzyl)-1,2,3,4,5,6,7,8-octahydro isoquinoline acetate seed crystal or a (R)-1-(4-methoxy benzyl)-1,2,3,4,5,6,7,8-octahydro isoquinoline acetate seed crystal into the solution 1, to obtain a solution 2; and (3) cooling the solution 2 to 0-5 DEG C, crystallizing to obtain (S)-1-(4-methoxy benzyl)-1,2,3,4,5,6,7,8-octahydro isoquinoline acetate or (R)-1-(4-methoxy benzyl)-1,2,3,4,5,6,7,8-octahydro isoquinoline acetate.

A process for preparing dextromethorphan method

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.

AN IMPROVED PROCESS FOR THE PREPARATION OF BUTORPHANOL TARTRATE

The present invention relates to an improved process for the preparation of Butorphanol tartrate of formula (I),

Racemization recycling method for byproduct in resolution mother liquor of dextromethorphan hydrobromide midbody

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.

General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

In the presence of a small amount of RuX2[(R)- or (S)-BINAP] (X = anionic ligand) a wide range of (Z)-2-acyl-1-benzylidene-1,2,3,4- tetrahydroisoquinolines are hydrogenated to give the saturated products in nearly quantitative yields and in high (up to 100%) optical yields. The enamide substrates are selectively prepared by N-acylation of the corresponding 1-benzylated 3,4-dihydroisoquinolines under suitable acylation conditions; some crystalline materials having low solubility are obtained by a second-order Z/E stereomutation technique utilizing the double-bond photolability and lattice energy effects. This asymmetric hydrogenation sets the key stereogenic center in a predictable manner, either R or S flexibly, at the C(1) position of the benzylated tetrahydroisoquinolines. The chiral products are converted by standard functional group modification to tetrahydropapaverine, laudanosine, tretoquinol, norreticuline, etc. Hydrogenation of the simple 1-methylene substrate is used for synthesis of salsolidine. This enantioselective hydrogenation is applied to the synthesis of morphine and its artificial analogues such as morphinans and benzomorphans of either chirality. A mnemonic device is presented for predicting the reactivity and enantiofacial selection of the BINAP-Ru catalyzed hydrogenation. Reaction with BINAP-Rh catalyst proceeds with a lower enantioselectivity and an opposite sense of asymmetric induction.