120157-94-0Relevant academic research and scientific papers
Sustainable and chemoselective N-Boc protection of amines in biodegradable deep eutectic solvent
Azizi, Najmedin,Shirdel, Fatemeh
, p. 1069 - 1074 (2017/05/12)
Abstract: A green and practical approach for the chemoselective N-tert-butyloxycarbonylation of structurally diverse amines with di-tert-butyl dicarbonate (Boc2O) is described. Selective N-Boc protection was achieved in excellent yields in urea-choline chloride deep eutectic solvent (DES) as the most promising environmentally benign and cost-effective solvent under mild reaction condition. DES can protect various aromatic and aliphatic amines using Boc2O in good to excellent yields in short reaction times without any side products. Graphical abstract: [Figure not available: see fulltext.].
4-Cyanobenzenesulfonamides: Amine Synthesis and Protecting Strategy To Compliment the Nosyl Group
Schmidt, Michael A.,Stokes, Ryjul W.,Davies, Merrill L.,Roberts, Frederick
, p. 4550 - 4560 (2017/05/12)
4-Cyanobenzenesulfonamides of secondary amines were found to cleave to the parent amine cleanly under the action of thiol and base. This feature readily lends itself to the use of this motif as an amine protecting/activating group within a broader context of amine synthesis. The crystalline sulfonamides could be further elaborated by alkylation and arylation similarly to nitrobenzenesulfonamides. The sulfonamides could withstand conditions that functionalize nitroarenes, such as reductions and vicarious nucleophilic substitution reactions.
Aqueous MW eco-friendly protocol for amino group protection
Nardi,Cano, N. Herrera,Costanzo,Oliverio,Sindona,Procopio
, p. 18751 - 18760 (2015/06/15)
In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.
N-Protection of amines using pyridinium 2,2,2-trifluoroacetate ionic liquid as an efficient and reusable catalyst
Karimian, Somaye,Tajik, Hassan
, p. 218 - 220 (2014/02/14)
A simple, green, and efficient method for the N-tert-butoxycarbonylation of amines by pyridinium 2,2,2-trifluoroacetate ([Py][OTf]) as an efficient and reusable catalyst is reported. In general, electron donating groups on aryl group give rise to the higher yields than electron withdrawing groups. Clean reaction, short reaction times, high yields, reusability of catalyst, and easy preparation of it are some advantages of this work.
The direct reductive amination of electron-deficient amines with aldehydes: The unique reactivity of the Re2O7 catalyst
Das, Braja Gopal,Ghorai, Prasanta
supporting information; experimental part, p. 8276 - 8278 (2012/09/22)
An unprecedented direct reductive amination of electron-deficient amines such as Cbz-, Boc-, EtOCO-, Fmoc-, Bz-, ArSO2-, Ar2PO-, etc. protected amines with aldehydes is achieved using the Re2O 7 catalyst and silanes as the hydride source. Excellent regioselective mono-alkylation and chemoselective reductive-amination were observed.
Suzuki-Miyaura cross-coupling reactions of potassium boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates
Molander, Gary A.,Shin, Inji
supporting information; experimental part, p. 3138 - 3141 (2012/08/07)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C-O activation of various mesylate derivatives to afford the corresponding products in moderate to good yields.
Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides
Molander, Gary A.,Shin, Inji
, p. 3956 - 3959 (2011/10/03)
Potassium Boc-protected aminomethyltrifluoroborate, a primary aminomethyl equivalent, was synthesized successfully through a "one-pot" process. With this trifluoroborate, Suzuki-Miyaura cross-coupling reactions were investigated with a variety of both aryl and hetaryl chlorides in good to excellent yields.
Facile preparation of protected benzylic and heteroarylmethyl amines via room temperature Curtius rearrangement
Leathen, Matthew L.,Peterson, Emily A.
supporting information; experimental part, p. 2888 - 2891 (2010/06/14)
A step-wise, room temperature procedure for acyl azide formation and the subsequent Curtius rearrangement of phenyl and heteroaryl acetic acids is described. We have developed a protocol for room temperature Curtius rearrangement in MeOH or CHCl3 that provides an improvement over standard conditions, avoiding the use of additives or heat. This room temperature optimization of the Curtius rearrangement prevents the formation of side products often observed with benzylic acids, allowing access to a variety of benzylic and heteroarylmethyl amines.
Preparation of enantiopure chiral amino- [D1]methyllithium compounds and determination of their micro- and macroscopic configurational stabilities
Kapeller, Dagmar C.,Hammerschmidt, Friedrich
experimental part, p. 5729 - 5739 (2009/12/29)
Chiral amino-[D1]methyllithiums have been tested with regard to their microscopic and macroscopic configurational stabilities. The N-Boc-N-diethoxyphosphinyl-sub-stituted analogue immediately rearranged, showing complete retention of configuration at up t
Versatile solid-phase synthesis of secondary amines from alcohols. Development of an N-Boc-(o-nitrobenzene)sulfonamide linker
Congreve, Miles S.,Kay, Corinne,Scicinski, Jan J.,Ley, Steven V.,Williams, Geoffrey,Murray, Peter J.,McKeown, Stephen C.,Watson, Stephen P.
, p. 4153 - 4156 (2007/10/03)
The development of a versatile amine releasing linker based on the modified o-nitrobenzene sulfonamide protective group is described. This new N-Boc-o-nitrobenzenesulfonamide (Boc-ONBS) linker enables the elaboration on resin of primary and secondary amines by sequential substitution of the sulfonamide moiety using the Mitsunobu reaction. A 16-member array of secondary and Boc protected primary amines was then prepared using this linker.
