3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt

Base Information

• Chemical Name: 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt
• CAS No.: 1545932-86-2
• Molecular Formula: C₇H₈O₃S*C₁₃H₂₂N₄
• Molecular Weight: 406.549
• Mol file: 1545932-86-2.mol

Synonyms:

Chemical Property of 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt

There total 12 articles about 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt 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: 92.0%

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane (423165-13-3) + toluene-4-sulfonic acid (104-15-4) → exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate (423165-08-6,1545932-86-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 50 ℃; under 2250.23 Torr; Solvent; Time; Inert atmosphere; Large scale;

DOI:10.1021/op800062d

Reference yield: 83.0%

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane (423165-13-3) + toluene-4-sulfonic acid (104-15-4) → 3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]octane p-toluenesulfonic acid salt (1545932-86-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20 ℃; for 12h; under 2585.81 Torr;

DOI:10.1021/op8000614

Reference yield:

8-Benzyl-1αH,5αH-nortropan-3-one Oxime (76272-34-9) → exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate (423165-08-6,1545932-86-2)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium; propan-1-ol / toluene / 12 h / Reflux; Inert atmosphere

2: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

3: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

4: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere

5: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere

7: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere

8: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere

With hydrogenchloride; propan-1-ol; phosphorus pentachloride; palladium 10% on activated carbon; hydrogen; sodium; sodium carbonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; tert-Amyl alcohol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/ml400370w

upstream raw materials:

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane

toluene-4-sulfonic acid

8-Benzyl-1αH,5αH-nortropan-3-one Oxime

exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester

Downstream raw materials:

4,4-difluoro-N-[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide

tert-butyl (1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropylcarbamate

C₃₃H₅₂N₈O

C₃₀H₄₆N₈O₄

Refernces

• 1、 Li, Dongmei,Tan, Yu,Peng, Lei,Li, Shan,Zhang, Nan,Liu, Yidong,Yan, Hailong. "Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy". supporting information. p. 4959 - 4963. Retrieved 2018/08/24.
• 2、 Zhao, Gui-Ling,Lin, Shuangzheng,Korotvicka, Ales,Deiana, Luca,Kullberg, Martin,Cordova, Armando. "Asymmetric synthesis of maraviroc (UK-427,857)". supporting information; experimental part. p. 2291 - 2298. Retrieved 2010/12/20.