74570-02-8

Upstream product

• 74570-02-8 (+)-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 93477-35-1 (+/-)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline hydrobromide 
• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 104-01-8 4-Methoxyphenylacetic acid 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 102558-14-5 (4-benzyloxy-phenyl)-acetic acid-(2-cyclohex-1-enyl-ethylamide) 
• 30356-07-1 (1S)-1-[(4-methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline 

Downstream Products

• 102558-09-8 4-((R)-2-benzyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 102666-11-5 4-((R)-2-phenethyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 67553-46-2 4-((R)-2-methyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 30356-08-2 (S)-1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxyphenyl)methyl]isoquinoline 
• 152-02-3 levallorphan 
• 67553-46-2 4-((S)-2-methyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 102558-09-8 4-((S)-2-benzyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 30356-07-1 (1S)-1-[(4-methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 125-73-5 (+)-dextrorphan 
• 94006-07-2 (S)-(+)-N-formyl-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 71-82-9 levallorphan tartarate 
• 806596-93-0 4-(5,6,7,8-tetrahydro-[1]isoquinolylmethyl)-phenol 
• 74570-02-8 4-((R)-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 74570-02-8 4-((S)-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 

Relevant academic research and scientific papers

Method for preparing levallorphan tartrate

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.

On the formation of a side product with hexahydroaporphine-like structure in the Grewe cyclization of dextromethorphan

Factors leading to the formation of a hexahydroaporphine-like cyclizing side product were studied systematically for the first time and the ratio of this side product was controlled effectively. To understand better the electronic effect of substrates on the formation of side products, different 1-benzyloctahydroisoquinolines with substituted groups on nitrogen or benzene ring were compared. A plausible mechanism of cyclizing reaction was proposed, and key intermediates as well as transition states were analyzed using DFT calculations.