Desmethylsertraline

Base Information

• Chemical Name: Desmethylsertraline
• CAS No.: 87857-41-8
• Molecular Formula: C16H15Cl2N
• Molecular Weight: 292.208
• European Community (EC) Number: 804-562-5
• UNII: CJJ71O9BE8
• DSSTox Substance ID: DTXSID60236666,DTXSID60904333
• Nikkaji Number: J258.553G
• Wikipedia: Desmethylsertraline
• Wikidata: Q5264613
• Metabolomics Workbench ID: 154776
• ChEMBL ID: CHEMBL40733
• Mol file: 87857-41-8.mol

Synonyms:CP 53261;CP 62508;CP-53261;CP-62508;desmethylsertraline;desmethylsertraline hydrochloride;N-demethylsertraline;N-desmethylsertraline;norsertraline

Chemical Property of Desmethylsertraline

Chemical Property:

• Vapor Pressure: 6.41E-07mmHg at 25°C
• Boiling Point: 409.6°C at 760 mmHg
• Flash Point: 201.5°C
• Density: 1.259g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 291.0581549
• Heavy Atom Count: 19
• Complexity: 309

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C2=CC=CC=C2C1C3=CC(=C(C=C3)Cl)Cl)N
• Isomeric SMILES: C1C[C@@H](C2=CC=CC=C2[C@@H]1C3=CC(=C(C=C3)Cl)Cl)N

Technology Process of Desmethylsertraline

There total 18 articles about Desmethylsertraline 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:

(R)-(+)-1-hydroxy-1,2-dihydronaphthalene (123849-23-0) → norsertraline (87857-41-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: Br₂; Et₃N / CH₂Cl₂

3: 510 mg / DBU / benzene / 20 °C

4: 55 percent / (MeCN)2PdCl₂; AsPh₃ / 1-methyl-pyrrolidin-2-one / 1.5 h / 80 °C

5: 98 percent / TBAF; AcOH / tetrahydrofuran

6: 88 percent / H₂ / [Ir(COD)(py)PCy₃]PF₆ / CH₂Cl₂ / 3 h / 51714.8 Torr

7: 88 percent / diphenylphosphorylazide; DBU / tetrahydrofuran / 0 - 20 °C

8: H₂ / Pd/C / ethanol / 1 h

With 1H-imidazole; dmap; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; bromine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; Crabtree's catalyst; triphenyl-arsane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; benzene; 1: Substitution / 2: Bromination / 3: Dehydrobromination / 4: Arylation / 5: Substitution / 6: Catalytic hydrogenation / 7: Substitution / 8: Catalytic hydrogenation;

DOI:10.1016/S0040-4020(99)00456-1

Reference yield:

(R)-1-tert-butyldiphenylsiloxy-1,2-dihydro-naphthalene (195388-52-4) → norsertraline (87857-41-8)

Guidance literature:

Multi-step reaction with 7 steps

1: Br₂; Et₃N / CH₂Cl₂

2: 510 mg / DBU / benzene / 20 °C

3: 55 percent / (MeCN)2PdCl₂; AsPh₃ / 1-methyl-pyrrolidin-2-one / 1.5 h / 80 °C

4: 98 percent / TBAF; AcOH / tetrahydrofuran

5: 88 percent / H₂ / [Ir(COD)(py)PCy₃]PF₆ / CH₂Cl₂ / 3 h / 51714.8 Torr

6: 88 percent / diphenylphosphorylazide; DBU / tetrahydrofuran / 0 - 20 °C

7: H₂ / Pd/C / ethanol / 1 h

With diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; bromine; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; Crabtree's catalyst; triphenyl-arsane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; benzene; 1: Bromination / 2: Dehydrobromination / 3: Arylation / 4: Substitution / 5: Catalytic hydrogenation / 6: Substitution / 7: Catalytic hydrogenation;

DOI:10.1016/S0040-4020(99)00456-1

Reference yield:

(R)-4-bromo-1-tert-butyldiphenylsiloxy-1,2-dihydro-naphthalene (195388-53-5) → norsertraline (87857-41-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / (MeCN)2PdCl₂; AsPh₃ / 1-methyl-pyrrolidin-2-one / 1.5 h / 80 °C

2: 98 percent / TBAF; AcOH / tetrahydrofuran

3: 88 percent / H₂ / [Ir(COD)(py)PCy₃]PF₆ / CH₂Cl₂ / 3 h / 51714.8 Torr

4: 88 percent / diphenylphosphorylazide; DBU / tetrahydrofuran / 0 - 20 °C

5: H₂ / Pd/C / ethanol / 1 h

With diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; Crabtree's catalyst; triphenyl-arsane; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; 1: Arylation / 2: Substitution / 3: Catalytic hydrogenation / 4: Substitution / 5: Catalytic hydrogenation;

DOI:10.1016/S0040-4020(99)00456-1

upstream raw materials:

(1S,4S)-1-azido-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalene

(1S,4S)-N,N-(dibenzyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

D-dibenzylaminophenylglycinal

(+)-(2R)-2-[bis(phenylmethyl)amino]-2-phenylethanol

Downstream raw materials:

Sertraline

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

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

Refernces

• 1、 Lautens, Mark,Rovis, Tomislav. "Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline". . p. 8967 - 8976. Retrieved 2007/10/03.