(E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester
• CAS No.: 81701-46-4
• Molecular Formula: C₂₄H₂₉NO₅
• Molecular Weight: 411.498
• Mol file: 81701-46-4.mol

Synonyms:(E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester

Chemical Property of (E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester

There total 2 articles about (E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester 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: 98.0%

methyl 4-bromo-3-methoxy-2-butenoate (35471-22-8) + benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium hydrobromide (5096-82-2) → (E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester (81701-46-4)

Guidance literature:

With zinc; In acetonitrile; at -15 - 20 ℃; for 48h;

DOI:10.1016/S0040-4039(00)97543-9

Reference yield: 98.0%

methyl 4-bromo-3-methoxy-2-butenoate (26536-93-6) + benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium hydrobromide (5096-82-2) → (E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester (81701-46-4)

Guidance literature:

With zinc; In acetonitrile; 1) cooling with an ice-salt bath -> room temperature, 5 h, 2) room temp., 2 days;

DOI:10.1021/jo00158a010

Reference yield:

(E)-4-(2-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-3-methoxy-but-2-enoic acid methyl ester (81701-46-4) → 5,6,9,10,11,11a-Hexahydro-2,3-dimethoxy-8,10-dioxo-8H-benzoquinolizine (5911-65-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 92 percent / 1/10 N aq. HCl / tetrahydrofuran

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)97543-9

upstream raw materials:

methyl 4-bromo-3-methoxy-2-butenoate

benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium hydrobromide

methyl 4-bromo-3-methoxy-2-butenoate

Downstream raw materials:

5,6,9,10,11,11a-Hexahydro-2,3-dimethoxy-8,10-dioxo-8H-benzoquinolizine

9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one