9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole]

Base Information

• Chemical Name: 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole]
• CAS No.: 1529806-84-5
• Molecular Formula: C₃₆H₃₅N₃O₄S₂
• Molecular Weight: 637.824
• Mol file: 1529806-84-5.mol

Synonyms:9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole]

Chemical Property of 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole]

There total 13 articles about 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole] 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: 84.0%

N-((1-benzyl-1H-indol-2-yl)methyl)-4-methyl-N-(3-(2-methyl-1-tosylaziridin-2-yl)prop-2-ynyl)benzenesulfonamide (1529806-65-2) → 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole] (1529806-84-5)

Guidance literature:

With triphenylphosphine gold(I)chloride; In dichloromethane; at 0 - 20 ℃; for 5h; Reagent/catalyst; Solvent; Time;

DOI:10.1016/j.tet.2013.11.084

Reference yield:

benzyl bromide (100-39-0) → 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole] (1529806-84-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.33 h / 0 °C

1.2: 1 h / 0 - 20 °C

2.1: n-butyllithium / diethyl ether / 3 h / 20 °C / Reflux

2.2: 3 h / Reflux

3.1: titanium(IV) tetraethanolate / toluene / 4 h / Reflux

4.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / 0 - 20 °C

5.1: triphenylphosphine; diethylazodicarboxylate / toluene / Inert atmosphere

6.1: triphenylphosphine gold(I)chloride / dichloromethane / 5 h / 0 - 20 °C

With titanium(IV) tetraethanolate; sodium tetrahydroborate; n-butyllithium; triphenylphosphine gold(I)chloride; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2013.11.084

Reference yield:

toluene-4-sulfonamide (70-55-3) → 9-benzyl-4'-methyl-1',2-ditosyl-1,1',2,3,5',9-hexahydro-spiro[pyrido[3,4-b]indole-4,2'-pyrrole] (1529806-84-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hydroxide / methanol / 10 °C

1.2: 3 h / 10 - 20 °C

2.1: tetrakis(acetonitrile)copper(I) perchlorate / acetonitrile / 0.25 h / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 0 °C

4.1: triphenylphosphine; diethylazodicarboxylate / toluene / Inert atmosphere

5.1: triphenylphosphine gold(I)chloride / dichloromethane / 5 h / 0 - 20 °C

With tetrakis(acetonitrile)copper(I) perchlorate; triphenylphosphine gold(I)chloride; tetrabutyl ammonium fluoride; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 4.1: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2013.11.084

upstream raw materials:

benzyl bromide

toluene-4-sulfonamide

N-((1-benzylindol-2-yl)methyl)-4-methylbenzenesulfonamide

3-(2-methyl-1-tosylaziridin-2-yl)prop-2-yn-1-ol