1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate

Base Information

• Chemical Name: 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate
• CAS No.: 1414540-31-0
• Molecular Formula: C₁₄H₂₃NO₆
• Molecular Weight: 301.34
• Mol file: 1414540-31-0.mol

Synonyms:1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate

Chemical Property of 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate

Chemical Property:

• Boiling Point: 371.3±42.0 °C(Predicted)
• Density: 1.170±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

cis-1-tert-Butyl2,4-diethylazetidine-1,2,4-tricarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate

There total 7 articles about 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate 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: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + 2,4-diethyl (2R,4S)-1-benzylazetidine-2,4-dicarboxylate (174309-28-5,1016233-19-4) → 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate (1414540-31-0)

Guidance literature:

With 20% Pd(OH)2/C; hydrogen; In ethanol; water; for 24h; under 3102.97 Torr;

DOI:10.1055/s-0032-1316748

Reference yield: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + C9H15NO4 → 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate (1414540-31-0)

Guidance literature:

In ethanol; for 24h; under 3102.97 Torr;

DOI:10.1016/j.tetlet.2012.08.156

Reference yield:

2,4-dibromoglutaric acid diethyl ester (870-78-0) → 1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate (1414540-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 10 h / 80 °C

2: 20% Pd(OH)2/C; hydrogen / ethanol; water / 24 h / 3102.97 Torr

With 20% Pd(OH)2/C; hydrogen; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0032-1316748

upstream raw materials:

gloutaric dichloride

2,4-dibromoglutaric acid diethyl ester

di-tert-butyl dicarbonate

2,4-diethyl (2R,4S)-1-benzylazetidine-2,4-dicarboxylate

Downstream raw materials:

tert-butyl 3-oxa-6-azabicyclo[3.1.1]heptane-1-carboxylate

3-oxa-6-azabicyclo[3.1.1]heptane 4-methylbenzenesulfonate

tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate

tert-butyl 3-[(2-nitrophenyl)sulfonyl]-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate

Refernces

• 1、 Walker, Daniel P.,Bedore, Matthew W.. "Concise synthesis of N3- and N6-monoprotected 3,6-diazabicyclo[3.1.1]heptanes; Useful intermediates for the preparation of novel bridged bicyclic piperazines". . p. 6332 - 6334. Retrieved 2013/01/15.