(S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate
• CAS No.: 1643565-08-5
• Molecular Formula: C₁₇H₂₂N₄O₂
• Molecular Weight: 314.387
• Mol file: 1643565-08-5.mol

Synonyms:(S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate

Chemical Property of (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate

There total 5 articles about (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate 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: 81.0%

(S)-tert-butyl 1-azidopropan-2-yl(prop-2-ynyl)carbamate + iodobenzene (591-50-4) → (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate (1643565-08-5)

Guidance literature:

iodobenzene; With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Inert atmosphere;

(S)-tert-butyl 1-azidopropan-2-yl(prop-2-ynyl)carbamate; With copper(l) iodide; In N,N-dimethyl-formamide; at 20 ℃; for 1.75h; Inert atmosphere; Heating;

DOI:10.1039/c4ob00639a

Reference yield:

(S)-N-(tert-butoxycarbonyl)alanine methyl ester (28875-17-4) → (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate (1643565-08-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

3.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

5.1: palladium diacetate; triphenylphosphine; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

5.2: 1.75 h / 20 °C / Inert atmosphere; Heating

With lithium aluminium tetrahydride; sodium azide; tetrabutylammomium bromide; palladium diacetate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c4ob00639a

Reference yield:

(S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane (84765-24-2) → (S)-tert-butyl 6-methyl-3-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate (1643565-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

3.1: palladium diacetate; triphenylphosphine; potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

3.2: 1.75 h / 20 °C / Inert atmosphere; Heating

With sodium azide; tetrabutylammomium bromide; palladium diacetate; sodium hydride; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c4ob00639a

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)alanine methyl ester

(S)-2-t-butoxycarbonylaminopropan-1-ol

(S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane

1-azido-(S)-2-(N-tert-butoxycarbonyl)aminopropane