Cinacalcet IMpurity 9

Base Information

• Chemical Name: Cinacalcet IMpurity 9
• CAS No.: 802918-36-1
• Molecular Formula: C₂₂H₂₄F₃N
• Molecular Weight: 359.434
• Mol file: 802918-36-1.mol

Synonyms:

Chemical Property of Cinacalcet IMpurity 9

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(αR)-5,6-Dihydro-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (αR)-5,6-Dihydro-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethanamine is synthetically prepared though a double bond migration in Heck reaction during the preparation of cinacalcet congeners. This enantiomerically pure material is seperated from its counter part, (αR)-7,8-Dihydro-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethanamine (D455330) using HPLC.

Technology Process of Cinacalcet IMpurity 9

There total 31 articles about Cinacalcet IMpurity 9 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: 78.0%

3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine (104774-87-0) + 1-(5,6-dihydro-naphthalen-1-yl)-ethanone (802918-49-6) → [1-(5,6-dihydronaphthalen-1-yl)ethyl]-[3-(3-trifluoromethylphenyl)propyl]amine (802918-47-4,802918-36-1)

Guidance literature:

3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine; 1-(5,6-dihydro-naphthalen-1-yl)-ethanone; With titanium(IV) isopropylate; at 20 ℃; Neat (no solvent);

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

Reference yield:

trans-3-(trifluoromethyl)cinnamoyl chloride (60689-14-7,64379-91-5) → [1-(5,6-dihydronaphthalen-1-yl)ethyl]-[3-(3-trifluoromethylphenyl)propyl]amine (802918-47-4,802918-36-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / NH₄OH / dioxane / 0 °C

2: 89 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

3: 65 percent / LAH / tetrahydrofuran / 4 h / Heating

4: Ti(OiPr)4

5: NaBH₄ / methanol

With titanium(IV) isopropylate; ammonium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1016/j.tetlet.2004.09.063

Reference yield:

trans-3-(trifluoromethyl)cinnamoyl chloride (60689-14-7,64379-91-5) → [(S)-1-(5,6-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine (802918-36-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / NH₄OH / dioxane / 0 °C

2: 89 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

3: 65 percent / LAH / tetrahydrofuran / 4 h / Heating

4: Ti(OiPr)4

5: NaBH₄ / methanol

6: Chirobiotic V / methanol; acetic acid; triethylamine

With titanium(IV) isopropylate; ammonium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; Chirobiotic V; hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; acetic acid; triethylamine;

DOI:10.1016/j.tetlet.2004.09.063

upstream raw materials:

1,2,3,4-tetrahydro-1,5-dihydroxy-naphthalene

5-Hydroxy-1-tetralone

3-(3-trifluoromethyl-phenyl)-propionic acid amide

trans-3-(trifluoromethyl)cinnamoyl chloride

Refernces

• 1、 Wang, Xin,Chen, Ying,Crockett, Richard,Briones, Jorge,Yan, Tony,Orihuela, Carlos,Zhi, Benxin,Ng, John. "Synthesis of Cinacalcet congeners". . p. 8355 - 8358. Retrieved 2007/10/03.