(1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 347384-85-4
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475

Synonyms:(1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

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Technology Process of (1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline

There total 1 articles about (1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)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: 45.0%

6,7,8-trimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-isoquinoline → (1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline (347384-85-4) + (1S)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:

With formic acid; triethylamine; Noyori's chiral ruthenium catalyst; In dichloromethane; at 20 ℃;

DOI:10.1021/jo010032k

Reference yield:

(1R)-6,7,8-trimethoxy-1-(3,4,5-trimethoxyphenyl)methyl-1,2,3,4-tetrahydroisoquinoline (347384-85-4) → (Z)-2-chloro-4-{3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-isoquinolinio]propyl}-1-{3-{(7S,13aR)-1,2,3,9,10,11-hexamethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]-7-quinolizinio}propyl}-butenedioate dichloride

Guidance literature:

Multi-step reaction with 6 steps

1.1: 65 percent / methanol; formic acid; H₂O / 2 h / Heating

2.1: NaI; Na₂CO₃ / butan-2-one / 48 h / Heating

2.2: Dowex-Cl^- / H₂O

3.1: 98 percent / 3 Angstroem molecular sieves / 1,2-dichloro-ethane / 72 h / 20 °C

4.1: 34 percent / DBU / acetonitrile / 0 - 20 °C

5.1: (COCl)2 / CH₂Cl₂; dimethylformamide / 2.5 h / 20 °C

6.1: 37 percent / CH₂Cl₂ / 20 °C

With oxalyl dichloride; 3 A molecular sieve; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In methanol; formic acid; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; butanone; 1.1: Pictet-Spengler cyclization;

DOI:10.1021/jo010032k

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