(1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane

Base Information

• Chemical Name: (1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane
• CAS No.: 286368-28-3
• Molecular Formula: C₁₆H₁₇IN₂O₂
• Molecular Weight: 396.228

Synonyms:(1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane

Chemical Property of (1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane

Chemical Property:

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Technology Process of (1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane

There total 2 articles about (1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane 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: 82.0%

Methanesulfonic acid (1S,2S,4S,5S)-5-(4-nitro-phenylethynyl)-1-aza-bicyclo[2.2.2]oct-2-ylmethyl ester (286368-27-2) → (1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane (286368-28-3)

Guidance literature:

With lithium iodide; In 1,4-dioxane; at 100 ℃;

DOI:10.1021/ol0057378

Reference yield:

[(1S,2S,4S,5S)-5-(4-Nitro-phenylethynyl)-1-aza-bicyclo[2.2.2]oct-2-yl]-methanol → (1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane (286368-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 20 °C

2: 82 percent / LiI / dioxane / 100 °C

With triethylamine; lithium iodide; In 1,4-dioxane; dichloromethane; 1: Substitution / 2: Substitution;

DOI:10.1021/ol0057378

Reference yield: 77.0%

(1S,2S,4S,5S)-2-iodomethyl-5-(p-nitrophenylethynyl)-1-azabicyclo[2.2.2]octane (286368-28-3) + methanol (67-56-1) → (1S,2R,5R,6S)-2-methoxy-6-(p-nitrophenylethynyl)-1-azabicyclo[3.2.2]nonane

Guidance literature:

With silver benzoate; at 50 ℃; for 20h;

DOI:10.1021/ol0057378

upstream raw materials:

Methanesulfonic acid (1S,2S,4S,5S)-5-(4-nitro-phenylethynyl)-1-aza-bicyclo[2.2.2]oct-2-ylmethyl ester

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