ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate

Base Information

• Chemical Name: ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate
• CAS No.: 89826-18-6
• Molecular Formula: C₁₈H₂₄O₂S
• Molecular Weight: 304.453
• Mol file: 89826-18-6.mol

Synonyms:ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate

Chemical Property of ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate

There total 8 articles about ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate 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: 92.0%

(1S,2S,3S,4R)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (89826-17-5) → ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate (89826-18-6)

Guidance literature:

With titanium(III) chloride; In ethanol; Ambient temperature;

DOI:10.1246/bcsj.61.467

Reference yield: 77.0%

(1S,2R,3S,4R)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (89764-39-6,89826-17-5,120410-03-9) → (1S,2R,3S,4R)-2-Methyl-3-p-tolylsulfanyl-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (89764-40-9,89826-18-6,108692-16-6)

Guidance literature:

With titanium(III) chloride; sodium acetate; In acetic acid;

DOI:10.1016/S0040-4039(01)91155-4

Reference yield:

2-oxo-propionic acid ethyl ester (617-35-6) → ethyl (+)-(1S,4R)-endo-2-methyl-3-(p-tolylthio)bicyclo<2.2.1>heptane-exo-2-carboxylate (89826-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 33 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / -80 °C

2: 31 percent / 5 h / 90 °C

3: 100 percent / 10percent Pd on carbon, H₂ / ethanol / Ambient temperature

4: 92 percent / 25percent aq. TiCl₃ / ethanol / Ambient temperature

With palladium on activated charcoal; n-butyllithium; titanium(III) chloride; hydrogen; In tetrahydrofuran; ethanol; hexane;

DOI:10.1246/bcsj.61.467

upstream raw materials:

(1S,2R,3S,4R)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

(1R,2R,3S,4S)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

(1R,2S,3S,4S)-2-Methyl-3-(toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

(1S,2S,3S,4R)-2-Methyl-3-((R)-toluene-4-sulfinyl)-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

Downstream raw materials:

(-)-(1S,4R)-endo-2-methyl-3-oxobicyclo<2.2.1>heptane-exo-2-carboxaldehyde