(+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE

Base Information

• Chemical Name: (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE
• CAS No.: 109620-49-7
• Molecular Formula: C₁₉H₂₆Cl₂N₂O*ClH
• Molecular Weight: 405.795
• Mol file: 109620-49-7.mol

Synonyms:

Chemical Property of (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE

Chemical Property:

• Storage Temp.: 2-8°C
• Solubility.: H2O: 11 mg/mL

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (+)-U-50488 Hydrochloride is a k-opioid agonist with no μ-opioid receptor effects in vitro, which may be used in the treatment of African trypanosomiasis.

Technology Process of (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE

There total 5 articles about (+)-TRANS-(1R,2R)-U-50488 HYDROCHLORIDE 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:

(+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol (69420-67-3) → U 50488 hydrochloride (67197-96-0,74512-83-7,109620-49-7,114358-63-3,114528-79-9,114528-81-3,121843-55-8)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

2: diethyl ether; water / 18 h / 10 - 20 °C / Inert atmosphere; Cooling with ice

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4: hydrogenchloride / diethyl ether; ethyl acetate / Inert atmosphere

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201100278

Reference yield:

trans-(+/-)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine (67198-34-9,67198-53-2,67347-43-7,99239-39-1,116301-06-5,121843-49-0,121843-50-3,121843-51-4,142434-12-6) → U 50488 hydrochloride (67197-96-0,74512-83-7,109620-49-7,114358-63-3,114528-79-9,114528-81-3,121843-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: hydrogenchloride / diethyl ether; ethyl acetate / Inert atmosphere

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201100278

Reference yield:

cyclohexane-1,2-epoxide (286-20-4) → U 50488 hydrochloride (67197-96-0,74512-83-7,109620-49-7,114358-63-3,114528-79-9,114528-81-3,121843-55-8)

Guidance literature:

Multi-step reaction with 5 steps

1: ethanol / 18 h / 80 °C / Inert atmosphere

2: triethylamine / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

3: diethyl ether; water / 18 h / 10 - 20 °C / Inert atmosphere; Cooling with ice

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

5: hydrogenchloride / diethyl ether; ethyl acetate / Inert atmosphere

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; ethanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201100278

upstream raw materials:

(+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol

cyclohexane-1,2-epoxide

Methanesulfonic acid (1R,2R)-2-pyrrolidin-1-yl-cyclohexyl ester

trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidynyl)-cyclohexyl]benzeneacetamide

Refernces