Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate

Base Information

• Chemical Name: Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate
• CAS No.: 444344-90-5
• Molecular Formula: C19H25NO4
• Molecular Weight: 331.412
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20442584
• Wikidata: Q82259940
• Mol file: 444344-90-5.mol

Synonyms:444344-90-5;Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate;ethyl 4-(((benzyloxy)carbonyl)amino)bicyclo[2.2.2]octane-1-carboxylate;ethyl 4-(phenylmethoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate;Ethyl 4-{[(benzyloxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate;SCHEMBL1308680;DTXSID20442584;MUYWBXXEGITRCE-UHFFFAOYSA-N;Ethyl4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate;ethyl 4-benzyloxycarbonylamino-bicyclo[2.2.2]octane-1-carboxylate;ethyl 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylate

Chemical Property of Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate

Chemical Property:

• PSA: 68.12000
• LogP: 3.77330
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 331.17835828
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C12CCC(CC1)(CC2)NC(=O)OCC3=CC=CC=C3

Technology Process of Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate

There total 4 articles about Ethyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-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:

4-(ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (834-50-4) → ethyl 4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylate (444344-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diphenylphosphoryl azide; Et₃N / toluene / 1 h / 20 °C

2: toluene / 0.75 h / Heating

3: 9.53 g / toluene / 18 h / Heating

With diphenylphosphoranyl azide; triethylamine; In toluene; 2: Curtius rearrangement;

DOI:10.1016/S0223-5234(01)01224-7

Reference yield:

ethyl iodide (75-03-6) + 4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylic acid (444344-91-6) → ethyl 4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylate (444344-90-5)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 50 - 60 ℃; for 8h;

Reference yield:

4-azidocarbonyl-bicyclo[2.2.2]octane-1-carboxylic acid ethyl ester → ethyl 4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylate (444344-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 0.75 h / Heating

2: 9.53 g / toluene / 18 h / Heating

In toluene; 1: Curtius rearrangement;

DOI:10.1016/S0223-5234(01)01224-7

upstream raw materials:

benzyl alcohol

4-(ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

ethyl iodide

4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylic acid

Downstream raw materials:

ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate

4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylic acid

N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester