(R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline
• CAS No.: 1198359-60-2
• Molecular Formula: C₃₁H₃₁NO₃
• Molecular Weight: 465.592
• Mol file: 1198359-60-2.mol

Synonyms:

Chemical Property of (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

There total 3 articles about (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline 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:

6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline (476159-11-2) + 4-benzyloxybenzyl chloride (836-42-0) → (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline (1198359-60-2) + (S)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 18h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/chem.200901477

Reference yield:

(R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2-dihydroquinoline → (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline (1198359-60-2) + (S)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; water; for 48h; Overall yield = 90 %; enantioselective reaction; Reflux;

DOI:10.1002/anie.201511663

Reference yield:

C24H22NO2(1+)*I(1-) + 4-methoxyphenylboronic acid (5720-07-0) → (R)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline (1198359-60-2) + (S)-1-(4-(benzyloxy)benzyl)-6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

Guidance literature:

Multi-step reaction with 2 steps

1: silver tetrafluoroborate; potassium phosphate tribasic trihydrate; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine) / acetonitrile / 12 h / 45 °C / Inert atmosphere

2: sodium acetate; toluene-4-sulfonic acid hydrazide / tetrahydrofuran; water / 48 h / Reflux

With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); silver tetrafluoroborate; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; potassium phosphate tribasic trihydrate; sodium acetate; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1002/anie.201511663

upstream raw materials:

6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline

4-benzyloxybenzyl chloride

4-methoxyphenylboronic acid