5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester
• CAS No.: 152362-59-9
• Molecular Formula: C₃₄H₃₃NO₅
• Molecular Weight: 535.64
• Mol file: 152362-59-9.mol

Synonyms:5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester

Chemical Property of 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester

There total 9 articles about 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl 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: 85.0%

diphenylacetic acid chloride (1871-76-7) + ethyl 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride → 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester (152362-59-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2015.07.018

Reference yield:

5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (1316755-16-4) + ethanol (64-17-5) → 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester (152362-59-9)

Guidance literature:

With thionyl chloride; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2015.07.018

Reference yield:

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester (152362-59-9)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / ethanol / 2 h / 100 °C / Inert atmosphere

2: diethyl amine hydrochloride / toluene / 12 h / 130 °C / Inert atmosphere; Dean-Stark

3: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 0 - 20 °C

4: zinc; acetic acid / 2 h / 60 - 65 °C

5: hydrogenchloride / water / 24 h / 20 °C / Inert atmosphere

6: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl amine hydrochloride; silica gel; potassium carbonate; acetic acid; triethylamine; zinc; In ethanol; dichloromethane; chloroform; water; isopropyl alcohol; toluene; 5: |Pictet-Spengler Synthesis;

DOI:10.1016/j.tet.2015.07.018

upstream raw materials:

3-methoxy-2-hydroxybenzaldehyde

2-benzyloxy-3-methoxybenzaldehyde

benzyl bromide

diphenylacetic acid chloride

Downstream raw materials:

5-(benzyloxy)-2-(2,2-diphenylacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

PD 126055

2-(2,2-diphenylacetyl)-5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester