ethyl 2-{[(tert-butoxy)carbonyl]amino}cyclopropane-1-carboxylate

Base Information

• Chemical Name: ethyl 2-{[(tert-butoxy)carbonyl]amino}cyclopropane-1-carboxylate
• CAS No.: 613261-19-1
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.27
• Hs Code.: 2924299090
• Mol file: 613261-19-1.mol

Synonyms:ethyl 2-{[(tert-butoxy)carbonyl]amino}cyclopropane-1-carboxylate

Chemical Property of ethyl 2-{[(tert-butoxy)carbonyl]amino}cyclopropane-1-carboxylate

Chemical Property:

• Boiling Point: 312.1±31.0 °C(Predicted)
• PKA: 11.98±0.40(Predicted)
• PSA: 68.12000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 1.66710

Purity/Quality:

97% ^*data from raw suppliers

Ethyl2-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 2-{[(tert-butoxy)carbonyl]amino}cyclopropane-1-carboxylate

There total 20 articles about ethyl 2-{[(tert-butoxy)carbonyl]amino}cyclopropane-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: 91.0%

diethyl-(1R,2R)-cyclopropane-1,2-dicarboxylate (31420-66-3,71666-05-2,149520-04-7) + tert-butyl alcohol (75-65-0) → (±)-cis-ethyl 2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate (613261-19-1)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In toluene; at 55 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.ejmech.2015.07.029

Reference yield: 54.0%

(±)-trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid (31420-66-3,71666-05-2,149520-04-7) + tert-butyl alcohol (75-65-0) → trans-ethyl 2-(tert-butoxycarbonylamino)-1-cyclopropane carboxylate (613261-19-1)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; for 6h; Heating;

DOI:10.1016/S0040-4020(01)89583-1

Reference yield:

diazoacetic acid ethyl ester (623-73-4) + t-butyl N-vinylcarbamate (7150-72-3) → ethyl (1R,2R)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate (613261-19-1) + ethyl (1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate (613261-19-1) + ethyl (1S,2S)-2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate (613261-19-1)

Guidance literature:

With C₂₃H₂₄N₅ORh⁽¹⁺⁾*F₆P^(1-); In dichloromethane; at 20 ℃; for 5h; Overall yield = 89 %; Overall yield = 42 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol303404c

upstream raw materials:

(±)-trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid

tert-butyl alcohol

diethyl trans-cyclopropane-1,2-dicarboxylate

(-)-(R,R)-cyclopropane-1,2-dicarboxylic acid ethyl ester

Downstream raw materials:

(+/-)-(1RS,2RS)-cis-<2-(tert.-butoxycarboamino)-cyclopropyl>-methanol