endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene

Base Information

• Chemical Name: endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene
• CAS No.: 135094-10-9
• Molecular Formula: C₁₇H₂₁NO₂
• Molecular Weight: 271.359
• Mol file: 135094-10-9.mol

Synonyms:endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene

Chemical Property of endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene

There total 7 articles about endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene 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: 74.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + ((R)-1-phenyl-ethylimino)-acetic acid ethyl ester (37662-05-8) → (1S,3S,4R)-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester (134984-63-7) + endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene (135094-10-9)

Guidance literature:

((R)-1-phenyl-ethylimino)-acetic acid ethyl ester; With trifluoroacetic acid; In dichloromethane; at -78 ℃; for 0.166667h;

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.166667h;

cyclopenta-1,3-diene; In dichloromethane; at -78 - 20 ℃; for 21h;

Reference yield: 64.7%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + ((R)-1-phenyl-ethylimino)-acetic acid ethyl ester (37662-05-8) → ethyl (1R,3S,4S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate + (1S,3S,4R)-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid ethyl ester (134984-63-7) + endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene (135094-10-9) + Ethyl (1R,3R,4S)-2-<(1R)-α-Phenylethyl>-2-azabicyclo<2.2.1>hept-5-ene-3-carboxylate (135635-58-4)

Guidance literature:

((R)-1-phenyl-ethylimino)-acetic acid ethyl ester; With chloro-trimethyl-silane; In methanol; toluene; at 0 - 5 ℃; for 2h;

cyclopenta-1,3-diene; In methanol; toluene; at -10 - 5 ℃; for 3h;

DOI:10.1021/op049828m

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → endo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.1>bicyclohept-5-ene (135094-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: PPTS / benzene / 2 h / Heating

2: BF₃*O(C₂H₅)2; TFA / -78 °C

With boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; trifluoroacetic acid; In benzene; 2: Diels-Alder reaction;

DOI:10.1016/j.bmcl.2005.12.046

upstream raw materials:

cyclopenta-1,3-diene

((R)-1-phenyl-ethylimino)-acetic acid ethyl ester

<(R)-(1-phenylethyl)imino>acetic acid ethyl ester

ethyl (E)-2-(α-methylbenzylimino)glyoxylate

Downstream raw materials:

(1R,4S)-3-(R)-carboethoxy-2-azabicyclo[2.2.1]heptane