56475-87-7Relevant articles and documents
A New Method for Introducing Some Active Methylene or Methine Groups to the 3-Position of Pyrrolidine or Piperidine Skeleton, and Its Application to Preparation of a Key Intermydiate for (+/-)-Eburnamonine Synthesis
Shono, Tatsuya,Matsumura, Yoshihiro,Ogaki, Masaru,Onomura, Osamu
, p. 1447 - 1450 (1987)
A new method for introducing a bis(methoxycarbonyl)methyl or 2-oxopropyl group to the 3-position of pyrrolidine or piperidine skeleton has been exploited, and this method could be used in the synthesis of a key intermediate for the (+/-)-eburnamonine synthesis.
Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy
Merx, Jona,Houthuijs, Kas J.,Elferink, Hidde,Witlox, Eva,Mecinovi?, Jasmin,Oomens, Jos,Martens, Jonathan,Boltje, Thomas J.,Rutjes, Floris P. J. T.
supporting information, (2022/01/06)
N-Acyliminium ions are highly reactive intermediates that are important for creating CC-bonds adjacent to nitrogen atoms. Here we report the characterization of cyclic N-acyliminium ions in the gas phase, generated by collision induced dissociation tandem mass spectrometry followed by infrared ion spectroscopy using the FELIX infrared free electron laser. Comparison of DFT calculated spectra with the experimentally observed IR spectra provided valuable insights in the conformations of the N-acyliminium ions.
Diastereoselective synthesis of 3-fluoro-2-substituted piperidines and pyrrolidines
Gichuhi, Paul N.,Kuriyama, Masami,Onomura, Osamu
, p. 331 - 346 (2014/01/17)
A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinate
A new and efficient synthesis of derivatives of octahydro-4H-pyrrolo[1,2-c] pyrido[1′,2′-a]imidazole
Rouchaud, Anne,Braekman, Jean-Claude
experimental part, p. 2346 - 2353 (2011/06/22)
When diethyl malonate was added to a solution of Δ1- piperideine, generated in situ by oxidative desamination and decarboxylation of L-lysine by N-bromosuccinimide (NBS), formation of the unexpected tricyclic compound 6 (4-diethylmalonyl-octahydro-4H-pyrrolo[1,2-c]pyrido[1′, 2′-a]imidazole)was observed. The structure of 6 was deduced from analysis of its spectroscopic data and was confirmed both by chemical degradation and by total synthesis. We proved that 3-bromo-1-piperideine was implicated in its formation. Moreover, based on this feature, a new and efficient synthesis of 6 was developed. The elaborated pathway was adapted to access derivatives related to 6 that differed in their C-4 substituent. A new and efficient synthesis of derivatives of the tricyclic heterocycle A from lysine is described. A mechanism involving 3-halopiperideines as intermediates and based on a ring contraction followed by Michael reaction is proposed and tested. Copyright
Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
Moriyama, Noriaki,Matsumura, Yoshihiro,Kuriyama, Masami,Onomura, Osamu
scheme or table, p. 2677 - 2687 (2010/04/29)
A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-pr
Stereoselective synthesis of azasugars by electrochemical oxidation
Furukubo, Shigeru,Moriyama, Noriaki,Onomura, Osamu,Matsumura, Yoshihiro
, p. 8177 - 8181 (2007/10/03)
A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-prote
A convenient method for synthesis of optically active methylphenidate from N-methoxycarbonylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction
Matsumura, Yoshihiro,Kanda, Yasuhisa,Shirai, Kimihiro,Onomura, Osamu,Maki, Toshihide
, p. 7411 - 7422 (2007/10/03)
A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding α-methoxylated carbamate utilizing electrochemical oxidation f
Reactivity of 2-Cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic Acid Esters Towards Various Nucleophiles: Regio- and Stereoselectivity of the Attack
Stanetty,Mihovilovic,Mereiter
, p. 1061 - 1072 (2007/10/03)
The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio- and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the
REGIOSELECTIVE INTRODUCTION OF ALKYL GROUPS TO THE POSITION α OR γ TO NITROGEN ATOM OF PIPERIDINE SKELETONS USING ANODIC OXIDATION IN A KEY STEP
Shono, Tatsuya,Terauchi, Jun,Ohki, Yoshihisa,Matsumura, Yoshihiro
, p. 6385 - 6386 (2007/10/02)
β,γ-Unsaturated N-alkoxycarbonyl-α-methoxypiperidines, which were prepared from N-alkoxypiperidines by using anodic oxidation in a key step, were regioselectively alkylated at the α-position by using Grignard reagents in the presence of BF3*Et2O, whereas in the presence of CuBr, the alkylation took place at the γ-position.
A NEW METHOD FOR REGIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 1-(METHOXYCARBONYL)-1,2-DIHYDROPYRIDINES
Shono, Tatsuya,Matsumura, Yoshihiro,Onomura, Osamu,Yamada, Yasufu
, p. 4073 - 4074 (2007/10/02)
2-Substituted 1,2-dihydropyridines including an optically active one were regioselctively prepared from 2-substituted piperidines through three intermediates, that is, (a) 1,2,3,4-tetrahydropyridines, (b) 5-bromo-6-methoxypiperidines, and (c) 1,2,3,4-tetrahydro-6-methoxypyridines.
