(1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Base Information

• Chemical Name: (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
• CAS No.: 258522-26-8
• Molecular Formula: C₂₈H₃₁NO₃
• Molecular Weight: 429.559
• Mol file: 258522-26-8.mol

Synonyms:(1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Chemical Property of (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

There total 12 articles about (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl 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: 70.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (5S)-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester (258522-25-7) → (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-26-8)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 0.5h;

(5S)-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4039(99)01874-2

Reference yield: 70.0%

Methylenetriphenylphosphorane (19493-09-5) + (5S)-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester (258522-25-7) → (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-26-8)

Guidance literature:

DOI:10.1016/S0040-4020(00)00227-1

Reference yield:

5,6,7,8-tetrahydro-2-methoxy-6-oxo-5-quinolinecarboxylic acid methyl ester (123435-97-2,130518-34-2) → (1S,9R)-5-Methoxy-11,13-dimethylene-6-aza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / p-toluenesulfonic acid monohydrate / benzene / 72 h / Heating

2: 75 percent / Pd(PPh₃)4; TMG / dioxane / 15 h / 20 °C

3: 70 percent

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; toluene-4-sulfonic acid; N,N,N',N'-tetramethylguanidine; In 1,4-dioxane; benzene; 1: Esterification / 2: Addition / 3: Substitution;

DOI:10.1016/S0040-4020(00)00227-1

upstream raw materials:

Methyltriphenylphosphonium bromide

(5S)-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester

Methylenetriphenylphosphorane

6-hydroxy-2-methylpyridine