(E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile

Base Information

• Chemical Name: (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile
• CAS No.: 318276-42-5
• Molecular Formula: C₂₅H₂₄N₄
• Molecular Weight: 380.492
• Mol file: 318276-42-5.mol

Synonyms:(E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile

Chemical Property of (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile

There total 5 articles about (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile 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:

diethyl 1-cyanomethylphosphonate (2537-48-6) + (1S,3S)-2-Benzyl-3-cyanomethyl-1-formylmethyl-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole (318276-43-6) → (Z)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile + (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile (318276-42-5)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

(1S,3S)-2-Benzyl-3-cyanomethyl-1-formylmethyl-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole; In N,N-dimethyl-formamide; at -20 ℃; for 1h;

DOI:10.1039/b005695m

Reference yield:

(1S,3S)-2-Benzyl-3-cyanomethyl-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (179939-64-1) → (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile (318276-42-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / NaH / dimethylformamide / 1.5 h / 0 - 20 °C

2.1: 83 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

3.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.33 h / -60 - 20 °C

4.1: NaH / dimethylformamide / 0.17 h / 0 °C

4.2: 108 mg / dimethylformamide / 1 h / -20 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.2: Horner-Wadsworth-Emmons alkylation;

DOI:10.1039/b005695m

Reference yield:

(1S,3S)-2-Benzyl-3-cyanomethyl-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole (179939-65-2) → (E)-4-((1S,3S)-2-Benzyl-3-cyanomethyl-9-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-but-2-enenitrile (318276-42-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 83 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

2.1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.33 h / -60 - 20 °C

3.1: NaH / dimethylformamide / 0.17 h / 0 °C

3.2: 108 mg / dimethylformamide / 1 h / -20 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.2: Horner-Wadsworth-Emmons alkylation;

DOI:10.1039/b005695m

upstream raw materials:

diethyl 1-cyanomethylphosphonate

(1S,3S)-2-Benzyl-3-cyanomethyl-1-formylmethyl-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole

(1S,3S)-2-Benzyl-3-cyanomethyl-1-(2-hydroxyethyl)-2,3,4,9-tetrahydro-9-methyl-1H-pyrido[3,4-b]indole

(1S,3S)-3-Cyanomethyl-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole