{(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]dec-2-yl}-methanol

Base Information

• Chemical Name: {(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]dec-2-yl}-methanol
• CAS No.: 1026623-01-7
• Molecular Formula: C₁₇H₂₀ClNO
• Molecular Weight: 289.805

Synonyms:{(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]dec-2-yl}-methanol

Chemical Property of {(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]dec-2-yl}-methanol

Chemical Property:

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Technology Process of {(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]dec-2-yl}-methanol

There total 2 articles about {(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.0^3,7]dec-2-yl}-methanol 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:

(1S,3S,6R,10S)-(Z)-9-(3-chlorobenzylidene)-7-azatricyclo[4.3.1.03,7]decane-10-carboxylic acid methyl ester (428854-65-3) → {(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]dec-2-yl}-methanol (1026623-01-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm0105373

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,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]dec-2-yl}-methanol (1026623-01-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (o-MeC₆H₄)3P; CuI / Pd₂(dba)3 / dimethylformamide / 0.25 h / 20 °C

1.2: dimethylformamide / 12 h / 45 - 50 °C

2.1: LiAlH₄ / tetrahydrofuran / 20 °C

With copper(l) iodide; lithium aluminium tetrahydride; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; 1.2: Stille coupling;

DOI:10.1021/jm0105373

Reference yield:

acetic anhydride (108-24-7) + {(1S,2S,3R,6S)-9-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-7-aza-tricyclo[4.3.1.03,7]dec-2-yl}-methanol (1026623-01-7) → (1S,3S,6R,10S)-(Z)-10-(acetoxymethyl)-9-(3-chlorobenzylidene)-7-azatricyclo[4.3.1.03,7]decane

Guidance literature:

With pyridine; dmap; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jm0105373

upstream raw materials:

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

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

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