(1R)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid ethyl ester

Base Information

• Chemical Name: (1R)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid ethyl ester
• CAS No.: 180468-41-1
• Molecular Formula: C18H19NO2
• Molecular Weight: 281.354
• Mol file: 180468-41-1.mol

Synonyms:(R)-1-Phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester;(1R)-ethyl 1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;(R)-ethyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate;

Chemical Property of (1R)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid ethyl ester

Chemical Property:

• PSA: 29.54000
• Density: 1.145
• LogP: 3.72850

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid ethyl ester

There total 7 articles about (1R)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic 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: 61.0%

(R)-2-(4-methoxybenzyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline + chloroformic acid ethyl ester (541-41-3) → ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (180468-41-1)

Guidance literature:

In toluene; at 100 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c00198

Reference yield:

1-phenyl-3,4-dihydroisoquinoline (52250-50-7) + diethyl dicarbonate (1609-47-8) → (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180468-42-2) + ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (180468-41-1)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-3,5-diMe-Synphos; hydrogen; In 1,4-dioxane; at 40 ℃; for 18h; under 22502.3 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol301281s

Reference yield:

chloroformic acid ethyl ester (541-41-3) + (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180272-45-1) → ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (180468-41-1)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃;

DOI:10.1021/jm050099q

upstream raw materials:

chloroformic acid ethyl ester

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

1-phenyl-3,4-dihydroisoquinoline

N-phenethylbenzamide

Downstream raw materials:

(3S)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate

(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate

Refernces

• 1、 Berhal, Farouk,Wu, Zi,Zhang, Zhaoguo,Ayad, Tahar,Ratovelomanana-Vidal, Virginie. "Enantioselective synthesis of 1-aryl-tetrahydroisoquinolines through iridium catalyzed asymmetric hydrogenation". supporting information; experimental part. p. 3308 - 3311. Retrieved 2012/08/28.