(R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 1316259-11-6
• Molecular Formula: C₁₈H₂₁NO₂
• Molecular Weight: 283.37
• Mol file: 1316259-11-6.mol

Synonyms:(R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

There total 21 articles about (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 36.0%

1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1277187-93-5) → (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1316259-11-6) + (S)-9-hydroxy-3-methoxyberbine (1316259-10-5)

Guidance literature:

With berberine bridge enzyme; tris hydrochloride; magnesium chloride; In toluene; at 40 ℃; for 24h; pH=9; optical yield given as %ee; enantioselective reaction; Darkness; Enzymatic reaction;

DOI:10.1021/jo201056f

Reference yield: 36.0%

1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1277187-93-5) → (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1316259-11-6) + C18H19NO2 + C18H19NO2

Guidance literature:

With berberine bridge enzyme; tris hydrochloride; magnesium chloride; catalase; In toluene; at 40 ℃; for 24h; pH=9; optical yield given as %ee; enantioselective reaction; Darkness; aq. buffer; Inert atmosphere; Enzymatic reaction;

DOI:10.1002/anie.201006268

Reference yield:

1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1277187-93-5) → (R)-1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1316259-11-6) + C18H21NO2 (1596345-17-3)

Guidance literature:

With Escherichia coli monoamine oxidase MAO-N D₁₁; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/anie.201400027

upstream raw materials:

2-(3-benzyloxyphenyl)-N-(3-methoxyphenethyl)-N-methylacetamide

1-(3-benzyloxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

1-(3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

m-hydroxyphenylacetic acid

Refernces

• 1、 Schrittwieser, Joerg H.,Groenendaal, Bas,Willies, Simon C.,Ghislieri, Diego,Rowles, Ian,Resch, Verena,Sattler, Johann H.,Fischereder, Eva-Maria,Grischek, Barbara,Lienhart, Wolf-Dieter,Turner, Nicholas J.,Kroutil, Wolfgang. "Deracemisation of benzylisoquinoline alkaloids employing monoamine oxidase variants". . p. 3657 - 3664. Retrieved 2015/02/05.
• 2、 Schrittwieser, Joerg H.,Resch, Verena,Wallner, Silvia,Lienhart, Wolf-Dieter,Sattler, Johann H.,Resch, Jasmin,MacHeroux, Peter,Kroutil, Wolfgang. "Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids". . p. 6703 - 6714. Retrieved 2011/10/18.