(R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 1316259-15-0
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.423
• Mol file: 1316259-15-0.mol

Synonyms:(R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-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)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

There total 20 articles about (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-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: 47.0%

1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1277187-96-8) → (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1316259-15-0) + C19H21NO5

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: 39.0%

1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1277187-96-8) → (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1316259-15-0) + (S)-9-hydroxy-1,2,3-trimethoxyberbine (1316259-14-9)

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:

3-benzyloxyphenylacetic acid (1860-58-8) → (R)-1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline (1316259-15-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / chloroform; water / 17 h / 0 - 20 °C

3.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere

3.2: 16 h / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen; acetic acid / methanol / 16 h / 20 °C

5.1: berberine bridge enzyme; tris hydrochloride; magnesium chloride; catalase / toluene / 24 h / 40 °C / pH 9 / Darkness; aq. buffer; Inert atmosphere; Enzymatic reaction

With oxalyl dichloride; berberine bridge enzyme; palladium 10% on activated carbon; hydrogen; tris hydrochloride; acetic acid; N,N-dimethyl-formamide; sodium hydroxide; magnesium chloride; catalase; trichlorophosphate; In methanol; chloroform; water; toluene; acetonitrile;

DOI:10.1002/anie.201006268

upstream raw materials:

2-(3-benzyloxyphenyl)-N-methyl-N-(3,4,5-trimethoxyphenethyl)acetamide

1-(3-benzyloxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

1-(3-hydroxybenzyl)-2-methyl-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline

m-hydroxyphenylacetic acid

Refernces

• 1、 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.