[(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester

Base Information

• Chemical Name: [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester
• CAS No.: 102939-73-1
• Molecular Formula: C₁₉H₂₀O₃
• Molecular Weight: 296.366
• Mol file: 102939-73-1.mol

Synonyms:[(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester

Chemical Property of [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester

There total 4 articles about [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic 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: 70.0%

(1S,4S,5R)-5-(2,2-Dibromo-vinyl)-5-(3-methoxy-benzyl)-bicyclo[2.2.1]hept-2-ene (102939-75-3) + methyl chloroformate (79-22-1) → [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester (102939-73-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)98658-1

Reference yield:

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (102939-69-5) → [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester (102939-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / Ph₃P / CH₂Cl₂ / 0 °C

2: 70 percent / n-buthyl-lithyum / tetrahydrofuran / -78 °C

With n-butyllithium; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)98658-1

Reference yield:

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbonitrile (102939-68-4) → [(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-en-2-yl]-propynoic acid methyl ester (102939-73-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / DIBAL-H / hexane; diethyl ether / 0 °C

2: 50 percent / Ph₃P / CH₂Cl₂ / 0 °C

3: 70 percent / n-buthyl-lithyum / tetrahydrofuran / -78 °C

With n-butyllithium; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4039(00)98658-1

upstream raw materials:

(1S,4S,5R)-5-(2,2-Dibromo-vinyl)-5-(3-methoxy-benzyl)-bicyclo[2.2.1]hept-2-ene

methyl chloroformate

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

(1S,2R,4S)-2-(3-Methoxy-benzyl)-bicyclo[2.2.1]hept-5-ene-2-carbonitrile

Downstream raw materials:

[(1R,2R,4S,5S,6S)-6-(3-Methoxy-benzyl)-3-oxa-tricyclo[3.2.1.0^2,4]oct-6-yl]-propynoic acid methyl ester