(1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester
• CAS No.: 428854-75-5
• Molecular Formula: C₁₈H₁₉ClINO₂
• Molecular Weight: 443.712

Synonyms:(1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester

Chemical Property of (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester

There total 4 articles about (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester 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:

2-chloro-1,4-diiodobenzene (79887-23-3) + (1S,3R,6S)-(Z)-9-[(tri-n-butylstannyl)methylene]-7-azatricyclo[4.3.1.03,7]decane-2β-carboxylic acid methyl ester (275355-50-5,275355-51-6) → (1S,2S,3R,6S)-9-Methylene-7-aza-tricyclo[4.3.1.03,7]decane-2-carboxylic acid methyl ester + (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.03,7]decane-10-carboxylic acid methyl ester (428854-75-5) + (1S,3S,6R,10S)-(Z)-9-(2-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.03,7]decane-10-carboxylic acid methyl ester

Guidance literature:

2-chloro-1,4-diiodobenzene; With copper(l) iodide; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

(1S,3R,6S)-(Z)-9-[(tri-n-butylstannyl)methylene]-7-azatricyclo[4.3.1.0^3,7]decane-2β-carboxylic acid methyl ester; In N,N-dimethyl-formamide; at 45 - 50 ℃; for 12h; Further stages.;

DOI:10.1021/jm0105373

Reference yield:

(1S,3S,6R,10S)-(Z)-9-(4-bromo-3-chlorobenzylidene)-7-azatricyclo[4.3.1.03,7]decane-10-carboxylic acid methyl ester (428854-74-4) → (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.03,7]decane-10-carboxylic acid methyl ester (428854-75-5)

Guidance literature:

(1S,3S,6R,10S)-(Z)-9-(4-bromo-3-chlorobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(tri-n-butyltin); In toluene; for 9h; Heating;

With iodine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/jm020596w

Reference yield:

(1S,3R,6S)-(Z)-9-[(tri-n-butylstannyl)methylene]-7-azatricyclo[4.3.1.03,7]decane-2β-carboxylic acid methyl ester (275355-50-5,275355-51-6) → (1S,3S,6R,10S)-(Z)-9-(3-chloro-4-iodobenzylidene)-7-azatricyclo[4.3.1.03,7]decane-10-carboxylic acid methyl ester (428854-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Ph₃As; Pd₂(dba)3; CuI / dimethylformamide / 0.33 h / 20 °C

1.2: dimethylformamide / 16 h / 45 - 55 °C

2.1: Bu₆Sn₂; Pd(PPh₃)4 / toluene / 9 h / Heating

2.2: I₂ / CH₂Cl₂ / 15 h / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenyl-arsane; bis(tri-n-butyltin); In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm020596w

upstream raw materials:

2-chloro-1,4-diiodobenzene

(1S,3R,6S)-(Z)-9-[(tri-n-butylstannyl)methylene]-7-azatricyclo[4.3.1.0^3,7]decane-2β-carboxylic acid methyl ester

(1S,3S,6R,10S)-(Z)-9-(4-bromo-3-chlorobenzylidene)-7-azatricyclo[4.3.1.0^3,7]decane-10-carboxylic acid methyl ester

1-bromo-2-chloro-4-iodobenzene

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