118207-34-4Relevant academic research and scientific papers
The effect of different amine bases in the Swern oxidation of β-amino alcohols
Chrisman, William,Singaram, Bakthan
, p. 2053 - 2056 (1997)
Swern oxidation of β-amino alcohols containing tertiary amino groups afforded the corresponding α-amino carbonyl compounds in fair to excellent yield. Yields were dependent on the steric requirement of the amine base used for the reaction and were optimiz
The Rabe amination after a century: Direct addition of N-heterocycles to carbonyl compounds
Scarpino Schietroma, Daniele M.,Monaco, Mattia R.,Bucalossi, Valerio,Walter, Philipp E.,Gentili, Patrizia,Bella, Marco
supporting information; experimental part, p. 4692 - 4695 (2012/08/08)
A catalytic version of the Rabe electrophilic amination is presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement.
Dynamic kinetic resolution allows a highly enantioselective synthesis of cis-α-aminocycloalkanols by ruthenium-catalyzed asymmetric hydrogenation
Liu, Sheng,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
, p. 7506 - 7508 (2008/09/17)
(Chemical Equation Presented) Resolutely dynamic hydrogenation: A highly efficient asymmetric hydrogenation of racemic N,N-disubstituted α-aminocycloalkanones involving dynamic kinetic resolution in the presence of a ruthenium catalyst gives chiral α-aminocycloalkanols with excellent enantioselectivities and cis diastereoselectivities (see scheme). A synthesis of optically pure U-(-)-50488 based on this reaction is reported.
NITROGEN-CONTAINING CYCLOHETERO CYCLOALKYLAMINOARYL DERIVATIVES FOR CNS DISORDERS
-
, (2008/06/13)
Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychotic disorders, convulsions and parkinsonism. Compounds of particular interest are of the formula STR1 wherein R 1 is selected from hydrido, loweralkyl, cycloalkylalkyl of four to six carbon atoms and loweralkenylloweralkyl; wherein each of R 2 and R 3 is independently selected from hydrido and loweralkyl; wherein each of R 4 through R 7, R 10 and R 11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is a number selected from four through six; wherein p is a number selected from zero through four; wherein q is a number selected from three through five; wherein A is selected from phenyl, naphthyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.
Synthesis and Receptor Binding of Enantiomeric N-Substituted cis-N--2-(1-pyrrolidinyl)cyclohexylamines as High-Affinity ? Receptor Ligands
Radesca, Lilian,Bowen, Wayne D.,Paolo, Lisa Di,Costa, Brian R. de
, p. 3058 - 3065 (2007/10/02)
N-Alkyl-substituted derivatives of (+)- and (-)-cis-N--2-(1-pyrrolidinyl)cyclohexylamine have been synthesized in nine steps in a stereospecific manner starting from cyclohexene oxide.The key step in the reaction sequence invo
Efficient Preparation of Cis Vicinal Tertiary Diamines from 2-Hydroxy Ketones in Two Steps
Fraenkel, Gideon,Gallucci, Judith,Rosenzweig, Howard S.
, p. 677 - 681 (2007/10/02)
Cyclic (C5 and C6) cis vicinal tertiary diamines are efficiently prepared by catalytic hydrogenation, Pd(C), of the corresponding N-substituted amino enamines, e.g. 6.The latter are obtained by p-toluenesulfonic acid catalyzed condensation of secondary amines with cyclic 2-hydroxy ketones in refluxing benzene under Dean-Stark conditions or from the N-substituted 2-amino ketones.For example cis-1,2-dipyrrolidinocyclohexane has been obtained from adipoin in 69percent overall yield, isolated.
