tert-Butyl aziridine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl aziridine-1-carboxylate
• CAS No.: 97308-23-1
• Molecular Formula: C7H13 N O2
• Molecular Weight: 143.18
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30579794
• Nikkaji Number: J575.931E
• Wikidata: Q82470416
• Mol file: 97308-23-1.mol

Synonyms:tert-Butyl aziridine-1-carboxylate;97308-23-1;N-(tert-butoxycarbonyl)aziridine;1-Aziridinecarboxylic acid, 1,1-dimethylethyl ester;n-boc-aziridine;N-Boc aziridine;1-Boc-aziridine;SCHEMBL698803;DTXSID30579794;tert-Butylaziridine-1-carboxylate;VBYPJHLRWKGNAI-UHFFFAOYSA-N;XDA30823;MFCD16036961;AKOS022182693;DS-15243;SY269903;CS-0079678;A915367

Chemical Property of tert-Butyl aziridine-1-carboxylate

Chemical Property:

• Boiling Point: 174.8±9.0 °C(Predicted)
• PKA: -3.23±0.20(Predicted)
• PSA: 29.31000
• Density: 1.088±0.06 g/cm3(Predicted)
• LogP: 1.17500
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

N-(tert-Butoxycarbonyl)aziridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC1
• Uses: N-(tert-Butoxycarbonyl)aziridine is a useful reagent for organic synthesis and other chemical processes. It is used as a reagent in the preparation of substituted indolines and carbazoles by benzyne-mediated cyclization-functionalization.

Technology Process of tert-Butyl aziridine-1-carboxylate

There total 3 articles about tert-Butyl aziridine-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: 98.0%

2-(tert-butoxycarbonylamino)ethyl methanesulfonate (96628-67-0) → tert-butyl 2-azidoethylcarbamate (117861-38-8) + N-(tert-butoxycarbonyl)aziridine (97308-23-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 0.0333333h; microwave irradiation;

Reference yield: 10.0%

2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5) → tert-butyl 3-(phenylsulfonyl)pyrrolidine-1-carboxylate + N-(tert-butoxycarbonyl)aziridine (97308-23-1)

Guidance literature:

With PVS; potassium tert-butylate; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03548

Reference yield:

4-Fluorophenol (371-41-5) + 2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2) → tert-butyl (2-(4-fluorophenoxy)ethyl)carbamate (263409-78-5) + N-(tert-butoxycarbonyl)aziridine (97308-23-1)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2006.04.149

upstream raw materials:

4-Fluorophenol

2-(N-tert-butoxycarbonylamino)ethanol

2-(tert-butoxycarbonylamino)ethyl methanesulfonate

2-(tert-butoxycarbonylamino)ethyl bromide

Downstream raw materials:

{2-[(2-Benzylsulfanyl-ethyl)-methyl-amino]-ethyl}-carbamic acid tert-butyl ester

(3,3,3-Triphenyl-propyl)-carbamic acid tert-butyl ester

1-(tert-butyl) 3-ethyl 2-oxopyrrolidine-1,3-dicarboxylate

{2-[(2-tert-Butoxycarbonylamino-ethyl)-(2-tritylsulfanyl-ethyl)-amino]-ethyl}-carbamic acid tert-butyl ester

Refernces

• 1、 Dener, Jeffrey M.,O'Bryan, Colin,Yee, Robert,Shelton, Emma J.,Sperandio, David,Mahajan, Tania,Palmer, James T.,Spencer, Jeffrey R.,Tong, Zhiwei. "Development of a scalable synthesis of a nonbasic inhibitor of the serine protease tryptase". . p. 4591 - 4595. Retrieved 2007/10/03.