51779-32-9Relevant articles and documents
Di-tert-butyl Ethynylimidodicarbonate as a General Synthon for the β-Aminoethylation of Organic Electrophiles: Application to the Formal Synthesis of Pyrrolidinoindoline Alkaloids (±)-CPC-1 and (±)-Alline
Beveridge, Ramsay E.,Hu, Yiwei,Gregoire, Bruce,Batey, Robert A.
, p. 8447 - 8461 (2020/07/16)
The reagent di-tert-butyl ethynylimidodicarbonate is demonstrated as a β-aminoethyl anion synthetic equivalent. It can be used to install ethyleneamine groups by exploiting its terminal alkyne reactivity with common organic electrophiles. Reactions exemplified with this terminal ynimide reagent include additions to imines, aldehydes, ketones, pyridinium salts, Michael acceptors, epoxides, and Pd-catalyzed Sonogashira couplings. Subsequent regioselective [3 + 2] cycloadditions of the alkynyl-imides (ynimides) generate N,N-di-Boc imide-functionalized triazole and isoxazole heterocycles. Reduction of the ynimides with Pd-catalyzed hydrogenation generates ethyleneimides with easily removable N,N-di-Boc-carbamate protecting groups, allowing for a flexible ynimide-based approach to ethyleneamine installation. The utility of this two-step aminoethylation strategy was demonstrated in the short formal syntheses of pyrrolidinoindoline alkaloids (±)-CPC-1 and (±)-alline. Analogously, the reagent (N,N,N′)-tri-Boc 2-ethynylhydrazine serves as a β-hydrazinoethyl anion synthetic equivalent.
Synthesis, Properties and Use of Nitridotricarbonic Acid Tri-tert-Butyl Ester
Degerbeck, Fredrik,Grehn, Leif,Ragnarsson, Ulf
, p. 896 - 898 (2007/10/02)
Exhaustive tert-butoxycarbonylation of Boc2NH with Boc2O-DMAP furnishes Boc3N in nearly quantitative yield.This stable compound is susceptible to nucleophiles and affords Boc2NH upon aminolysis.The properties of Boc3N have been exploited in a practical one-pot procedure for the synthesis of Boc2NH from NH4Cl, which is particularly economical in the preparation of Boc215NH.
Synthesis of Analogues of γ-Aminobutyric Acid. Part 11. Unsaturated and Saturated Tetronic Acid Derivatives
Allan, Robin D.,Johnston, Graham A. R.,Kazlauskas, Rymantas,Tran, Hue W.
, p. 2983 - 2986 (2007/10/02)
5-(2-Aminoethylidene)-4-hydroxyfuran-2(5H)-one (3) and the corresponding reduced 5-(2-aminoethyl) derivative (4) have been synthesised as conformationally restricted analogues of the neurotransmitter GABA.The use of the t-butyl protected reagents bis(t-butoxycarbonyl)amine and 5-ethylidene-4-t-butoxyfuran-2(5H)-one (7b) allowed generation of the required amino compounds under mild acidic deprotection conditions in the final step.