cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Base Information

• Chemical Name: cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine
• CAS No.: 267884-85-5
• Molecular Formula: C₂₂H₂₅Cl₂NO₂
• Molecular Weight: 406.352
• Mol file: 267884-85-5.mol

Synonyms:cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Chemical Property of cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

There total 23 articles about cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 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%

4(S)-(3,4-dichlorophenyl)-3,4-dihydro-N-methyl-1(2H)-naphthalenimine (1186422-36-5) + di-tert-butyl dicarbonate (24424-99-5) → cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (267884-85-5)

Guidance literature:

With C₄₃H₃₀BF₁₅N₂O₂RuS; hydrogen; In 1,2-dichloro-ethane; at 40 ℃; for 10h; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1016/j.tet.2012.03.019

Reference yield: 98.0%

(S)-N-(4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)methanamine (312620-93-2) + di-tert-butyl dicarbonate (24424-99-5) → cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (267884-85-5)

Guidance literature:

With RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen; In 1,2-dichloro-ethane; at 40 ℃; for 10h; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Autoclave;

DOI:10.1002/chem.201002846

Reference yield: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + sertraline hydrochloride (79559-97-0) → cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (267884-85-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.33333h; Inert atmosphere;

DOI:10.1021/jacs.7b07661

upstream raw materials:

cis-(1S,4S)-N-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

methyl iodide

di-tert-butyl dicarbonate

D-dibenzylaminophenylglycinal

Downstream raw materials:

sertraline hydrochloride

Sertraline

Refernces

• 1、 Chen, Fei,Ding, Ziyuan,He, Yanmei,Qin, Jie,Wang, Tianli,Fan, Qing-Hua. "Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope". . p. 5248 - 5257. Retrieved 2012/08/08.
• 2、 Chandrasekhar,Venkat Reddy. "An expedient total synthesis of cis-(+)-sertraline from D-phenylglycine". . p. 1111 - 1114. Retrieved 2007/10/03.