ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Base Information

• Chemical Name: ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• CAS No.: 1147826-04-7
• Molecular Formula: C₁₆H₁₉NO₃S
• Molecular Weight: 305.398

Synonyms:ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Chemical Property of ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

There total 1 articles about ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-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:

ethyl (S)-N-(p-toluenesulfinyl)iminoacetate + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (1147826-04-7) + ethyl (1R,3S,4S,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate + ethyl (1R,3R,4S,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 17h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.090

Reference yield: 46.0%

ethyl (1S,3S,4R,S(S))-2-(p-tolylsulfinyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (1147826-04-7) → (1S,3S,4R)-N-Tosyl-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; for 2.5h; optical yield given as %ee; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.090

upstream raw materials:

cyclopenta-1,3-diene

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