Tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate
• CAS No.: 178311-48-3
• Molecular Formula: C12H23N3O2
• Molecular Weight: 241.33000
• European Community (EC) Number: 850-959-1
• DSSTox Substance ID: DTXSID60598352
• Wikidata: Q72510429
• Mol file: 178311-48-3.mol

Synonyms:178311-48-3;tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate;1-(TERT-BUTOXYCARBONYL)-3-(1-PIPERAZINYL)AZETIDINE;1-N-Boc-3-(1-piperazine)azetidine;tert-butyl 3-piperazin-1-ylazetidine-1-carboxylate;1-Azetidinecarboxylic acid, 3-(1-piperazinyl)-, 1,1-dimethylethyl ester;MFCD09264407;SCHEMBL2550653;DTXSID60598352;KEQBTRKQDYXHTO-UHFFFAOYSA-N;1-(1-Boc-3-azetidinyl)piperazine;AMY23126;1-Boc-3-(piperazin-1-yl)azetidine;AKOS016353068;SB34357;SY308209;DB-065218;CS-0020809;EN300-95702;A26784;D85602;1-(t-Butoxycarbonyl)-3-(piperazin-1-yl)azetidine;A812355;tert-butyl3-(piperazin-1-yl)azetidine-1-carboxylate;F2147-2382;Z1270443746;3-(1-piperazinyl)-1-azetidinecarboxylic acid tert-butyl ester;3-piperazin-1-yl-azetidine-1-carboxylic acid tert-butyl ester

Chemical Property of Tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate

Chemical Property:

• Boiling Point: 337.3±37.0 °C(Predicted)
• PKA: 9.12±0.10(Predicted)
• PSA: 44.81000
• Density: 1.115
• LogP: 0.71550
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 241.17902698
• Heavy Atom Count: 17
• Complexity: 276

Purity/Quality:

99%+, ^*data from raw suppliers

1-N-Boc-3-(1-piperazine)azetidine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C1)N2CCNCC2
• Uses: tert-Butyl 3-(piperazin-1-yl)azetidine-1-carboxylate dihydrochloride is used as a reactant in the preparation of allele-specific inhibitors that inactivate mutant KRAS G12C by a trapping mechanism.

Technology Process of Tert-butyl 3-(piperazin-1-yl)azetidine-1-carboxylate

There total 7 articles about Tert-butyl 3-(piperazin-1-yl)azetidine-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: 87.0%

benzyl 4-(1-(tert-butoxycarbonyl)azetidin-3-yl)piperazine-1-carboxylate → 1-(Tert-butoxycarbonyl)-3-(1-piperazinyl)azetidine (178311-48-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 25 ℃; for 20h;

Reference yield:

piperazine (110-85-0) + 3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester (141699-58-3) → 1-(Tert-butoxycarbonyl)-3-(1-piperazinyl)azetidine (178311-48-3)

Guidance literature:

In dichloromethane;

Reference yield:

tert-butyl 3-oxoazetidine-1-carboxylate (398489-26-4) → 1-(Tert-butoxycarbonyl)-3-(1-piperazinyl)azetidine (178311-48-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / methanol / 1 h / 25 °C

1.2: 16 h / 25 °C

2.1: hydrogen; palladium 10% on activated carbon / methanol / 20 h / 25 °C

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol;

upstream raw materials:

piperazine

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

tert-butyl 3-oxoazetidine-1-carboxylate

Refernces

• 1、 -. "MODULATORS OF PROTEOLYSIS AND ASSOCIATED METHODS OF USE". . . Retrieved 2019/10/29.
• 2、 -. "(Azetidin-1-ylalkyl) lactams as tachykinin antagonists". . . Retrieved 2008/06/13.