7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 15357-95-6
• Molecular Formula: C₁₇H₁₉NO₂
• Molecular Weight: 269.343
• Mol file: 15357-95-6.mol

Synonyms:7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property of 7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

There total 7 articles about 7-(benzyloxy)-6-methoxy-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: 87.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine (22231-61-4) → 7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (15357-95-6)

Guidance literature:

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine; With formic acid; at 0 ℃; for 0.25h;

formaldehyd; at 50 ℃; for 12h;

DOI:10.1021/acsmedchemlett.8b00229

Reference yield: 77.0%

7-benzyloxy-6-methoxy-3,4-dihydroisoquinoline hydrochloride → 7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (15357-95-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 15 - 20 ℃; Inert atmosphere;

DOI:10.3998/ark.5550190.0012.514

Reference yield:

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) → 7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (15357-95-6)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; ammonium acetate / 1.5 h / Heating

2: lithium aluminum hydride / tetrahydrofuran / 12 h / Heating

3: formic acid / 12 h / Heating

With ammonium acetate; lithium aluminium tetrahydride; formic acid; acetic acid; In tetrahydrofuran; 1: Henry condensation / 3: Pictet-Spengler cyclization;

DOI:10.1016/S0040-4020(02)00010-8

upstream raw materials:

formaldehyd

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine

3-methoxy-4-(phenylmethoxy)benzaldehyde

3-methoxy-4-benzyloxy-ω-nitrostyrolene

Downstream raw materials:

7-(benzyloxy)-2-[(4R)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline

(S)-1-(4-methoxymethoxybenzyl)-2-methyl-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline

2-[4,5-dihydro-4-((R)-1-methylethyl)-2-oxazolyl]-(S)-1-(4-methoxymethoxybenzyl)-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline

(S)-1-(4-methoxymethoxybenzyl)-2-formyl-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Ronson, Thomas O.,Kitsiou, Christiana,Unsworth, William P.,Taylor, Richard J.K.. "Synthetic approaches to pallimamine and analogues using direct imine acylation". . p. 6099 - 6106. Retrieved 2016/09/14.
• 2、 Cutter, Paul S,Miller, R.Bryan,Schore, Neil E. "Synthesis of protoberberines using a silyl-directed Pictet-Spengler cyclization". . p. 1471 - 1478. Retrieved 2007/10/03.