3-Ethoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-Ethoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1002355-96-5
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.287
• Hs Code.: 2933990090
• Mol file: 1002355-96-5.mol

Synonyms:3-Ethoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester;1-Boc-3-ethoxycarbonylMethylene-azetidine;tert-Butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate 95%

Chemical Property of 3-Ethoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• Refractive Index: n20/D1.474
• Boiling Point: 319.5±35.0 °C(Predicted)
• PKA: -1.67±0.20(Predicted)
• Flash Point: >110℃
• PSA: 55.84000
• Density: 1.188
• LogP: 1.66450
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Building block used as a precursor to the synthesis of thia and oxa-azaspiro[3.4]octanes. As reported in the Carreira lab, the product can readily undergo [3+2] cycloadditions with dipolariphiles to generate a series of small-ring spirocycles.

Technology Process of 3-Ethoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester

There total 4 articles about 3-Ethoxycarbonylmethylene-azetidine-1-carboxylic acid tert-butyl ester 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: 100.0%

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate (1002355-96-5)

Guidance literature:

In dichloromethane; for 6h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1021/ol402127b

Reference yield: 92.0%

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate (1002355-96-5)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h;

tert-butyl 3-oxoazetidine-1-carboxylate; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h;

Reference yield: 78.4%

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) + triethyl phosphonoacetate → tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate (1002355-96-5)

Guidance literature:

tert-butyl 3-oxoazetidine-1-carboxylate; With sodium hydride; In tetrahydrofuran; at 0 ℃;

triethyl phosphonoacetate; In tetrahydrofuran; at 20 ℃; for 2h;

upstream raw materials:

tert-butyl 3-oxoazetidine-1-carboxylate

diethoxyphosphoryl-acetic acid ethyl ester

ethyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

tert-butyl 3-(3-bromophenyl)-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

C₁₁H₁₇NO₃S

C₁₉H₂₆N₂O₆S

tert-butyl 7-amino-5-thia-2-azaspiro[3.4]octane-2-carboxylate 5,5-dioxide

Refernces

• 1、 Malashchuk, Andrii,Chernykh, Anton V.,Perebyinis, Mariana Y.,Komarov, Igor V.,Grygorenko, Oleksandr O.. "Monoprotected Diamines Derived from 1,5-Disubstituted (Aza)spiro[2.3]hexane Scaffolds". . p. 6570 - 6579. Retrieved 2021/03/03.
• 2、 Bai, Guoyun,Brodney, Michael A.,Brown, Matthew F.,Butler, Christopher R.,Czabaniuk, Lara C.,Gilbert, Adam M.,Lachapelle, Erik A.,Li, Chao,McAllister, Laura A.,O'Connell, Thomas N.,Ogilvie, Kevin,Philippe, Laurence,Salomon-Ferrer, Romelia,Shapiro, Michael J.,Starr, Jeremy T.,Uccello, Daniel P.,Withka, Jane M.,Yan, Jiangli. "Intramolecular Ring-Opening Decomposition of Aryl Azetidines". supporting information. p. 1585 - 1588. Retrieved 2021/10/21.