tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate
• CAS No.: 73286-70-1
• Molecular Formula: C9H15NO2
• Molecular Weight: 169.224
• Hs Code.: 29339900
• European Community (EC) Number: 615-949-1
• DSSTox Substance ID: DTXSID60408785
• Nikkaji Number: J1.080.525B
• Mol file: 73286-70-1.mol

Synonyms:73286-70-1;tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate;N-Boc-3-Pyrroline;N-Boc-2,5-dihydropyrrole;Tert-butyl 2,5-dihydropyrrole-1-carboxylate;1-Boc-2,5-dihydro-1H-pyrrole;N-Boc-2,5-dihydro-1H-pyrrole;tert-butyl 2H-pyrrole-1(5H)-carboxylate;MFCD01863512;2,5-Dihydro-pyrrole-1-carboxylic acid tert-butyl ester;1H-PYRROLE-1-CARBOXYLIC ACID, 2,5-DIHYDRO-, 1,1-DIMETHYLETHYL ESTER;tert-butyl-2,5-dihydro-1H-pyrrole-1-carboxylate;SCHEMBL222920;N-t-butoxycarbonyl-3-pyrroline;1-t-butoxycarbonyl-3-pyrroline;2,5-Dihydropyrrole-1-carboxylic acid tert-butyl ester;DTXSID60408785;1-tert-butoxycarbonyl-3-pyrroline;CHEBI:194984;N-(t-butoxycarbonyl)-3-pyrroline;YEBDZDMYLQHGGZ-UHFFFAOYSA-N;1-BOC-2,5-DIHYDROPYRROLE;BCP24358;CS-D0811;N-(tert-Butoxycarbonyl)-3-pyrroline;tert-Butyl 3-pyrroline-1-carboxylate;AKOS005145537;AKOS025243463;PB34003;PS-3886;N-Boc-2,5-dihydro-1H-pyrrole, 96%;1-tert-Butoxycarbonyl-2,5-dihydropyrrole;BP-13132;A9467;AM20100702;B3735;FT-0649578;EN300-50372;tert-butyl 2,5-dihydro-1H-pyrrole-l-carboxylate;A927921;W-203671;1,1-dimethylethyl 2,5-dihydro-1H-pyrrole-1-carboxylate;2,5-dihydro-pyrrole-1 -carboxylic acid tert-butyl ester;F0001-1854;TERT-BUTYL2,5-DIHYDRO-1H-PYRROLE-1-CARBOXYLATE;Z600434690;2-Methyl-2-propanyl 2,5-dihydro-1H-pyrrole-1-carboxylate;2,5-Dihydro-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester

Chemical Property of tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Chemical Property:

• Appearance/Colour: White to yellow low melting solid or liquid
• Vapor Pressure: 0.058mmHg at 25°C
• Melting Point: 40.0 to 44.0 °C
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 219.889 °C at 760 mmHg
• PKA: -1.46±0.20(Predicted)
• Flash Point: 86.786 °C
• PSA: 29.54000
• Density: 1.056 g/cm³
• LogP: 1.73120
• Storage Temp.: Room temperature.
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 169.110278721
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl-3-pyrroline-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC=CC1
• Uses: Used in a synthesis of ?-aryl-GABA analogues by Heck arylation with arenediazonium salts, as well as synthesize aryl pyrrolizidines. N-Boc-pyrroline has also been utilized in the synthesis of various antibacterial compounds. It has also been used in the preparation of regioisomeric 3-hydroxyisoxazolinyl prolines which are medicinally active.

Technology Process of tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

There total 29 articles about tert-Butyl 2,5-dihydro-1H-pyrrole-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: 100.0%

3-Pyrroline (109-96-6,760178-50-5) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-3-pyrroline (73286-70-1)

Guidance literature:

In tetrahydrofuran; water; at 0 - 20 ℃; for 3.16667h;

Reference yield: 99.0%

tert-butyl diallylcarbamate (151259-38-0) → N-(tert-butoxycarbonyl)-3-pyrroline (73286-70-1)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 50 ℃; for 8h; Glove box;

DOI:10.1021/ol9029808

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + 2,5-dihydro-1H-pyrrole hydrochloride (63468-63-3) → N-(tert-butoxycarbonyl)-3-pyrroline (73286-70-1)

Guidance literature:

With sodium hydrogencarbonate; In water; at 0 - 25 ℃; for 10h; Reagent/catalyst; Temperature;

upstream raw materials:

3-Pyrroline

N-(tert-butyloxycarbonyl) azide

di-tert-butyl dicarbonate

tert-butyl diallylcarbamate

Downstream raw materials:

4-(3,4-dimethoxy-phenyl)-2-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate

trans tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate

tert-butyl 3-(2,5-difluorophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate

Refernces

• 1、 Zhao, Huaibo,McMillan, Alastair J.,Constantin, Timothée,Mykura, Rory C.,Juliá, Fabio,Leonori, Daniele. "Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins". supporting information. p. 14806 - 14813. Retrieved 2021/09/18.
• 2、 Kumar, Gollapudi Ravi,Murthy Boddapati,Meruga, Santha Kumari,Bollikolla, Hari Babu. "Synthesis of new (±)-1-(4-(3-fluorobenzyloxy)pyrrolidin-3-yl)-4-phenyl-1H-1,2,3-triazole derivatives via click reaction and study of anti-cancer activity against HCT 116, MDA-MB231, Mia-PaCa2 cell lines". . p. 2813 - 2825. Retrieved 2020/10/06.