125224-43-3Relevant articles and documents
Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (-)-paroxetine
Nemoto, Tetsuhiro,Sakamoto, Tatsurou,Fukuyama, Takashi,Hamada, Yasumasa
, p. 4977 - 4981 (2008/02/09)
An Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxide is described. Asymmetric allylic alkylation of terminal allylic carbonates proceeded using 5 mol % of Ir catalyst, 5 mol % of DIAPHOX 1i, 10 mol % of NaPF6, 10 mo
A new route to 3,4-disubstituted piperidines: Formal synthesis of (-)-paroxetine and (+)-femoxetine
Yamada, Shinji,Jahan, Ishrat
, p. 8673 - 8676 (2007/10/03)
A new route to 3,4-disubstituted piperidines was developed using chiral 1,4-dihydropyridines as key intermediates, the synthetic utility of which was demonstrated by formal synthesis of (-)-paroxetine and (+)-femoxetine.
Catalytic enantioselective conjugate reduction of lactones and lactams
Hughes, Gregory,Kimura, Masanari,Buchwald, Stephen L.
, p. 11253 - 11258 (2007/10/03)
A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of α,β-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl2·H2O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.
Enantioselective Michael additions to α,β-unsaturated imides catalyzed by a salen-al complex
Taylor, Mark S.,Jacobsen, Eric N.
, p. 11204 - 11205 (2007/10/03)
(Salen)aluminum complex 1b is an efficient catalyst for the conjugate addition of di- and trisubstituted nitriles to a wide range of acyclic alkyl- and aryl-substituted α,β-unsaturated imides. This new methodology provides access to multifunctional compounds that previously have not been readily accessible in enantioenriched form. Synthetic applications of these products include the preparation of enantiomerically enriched piperidines, as exemplified by an expedient asymmetric catalytic synthesis of (-)-paroxetine. Copyright
Optically pure paroxetine precursors
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, (2008/06/13)
A biocatalytic process to obtain optically enriched derivatives of trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidines, based on the enzymatic resolution of racemic precursors of formula III (where R3 is preferably phenyl or benzyl) by acylatio
Enzymatic resolution of trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines, key intermediates in the synthesis of (-)-Paroxetine
De Gonzalo,Brieva,Sanchez,Bayod,Gotor
, p. 8947 - 8953 (2007/10/03)
Two Candida antarctica lipases catalyze the enantioselective acylation of N-substituted trans-4-(4′-fluorophenyl)-3-hydroxymethylpiperidines in organic solvents. These two lipases show opposite stereochemical preference in these processes. Both enantiomers can be obtained in their optically pure forms. The (3S,4R) isomer, is an intermediate for the synthesis of (-)-Paroxetine.
Improved synthesis of paroxetine hydrochloride propan-2-ol solvate through one of metabolites in humans, and characterization of the solvate crystals
Sugi, Kiyoshi,Itaya, Nobushige,Katsura, Tadashi,Igi, Masami,Yamazaki, Shigeya,Ishibashi, Taro,Yamaoka, Teiji,Kawada, Yoshihiro,Tagami, Yayoi,Otsuki, Michiya,Ohshima, Takao
, p. 529 - 536 (2007/10/03)
Paroxetine, a potent and selective inhibitor of 5-hydroxytryptamine (serotonin) uptake, was prepared through a piperidine derivative, which was reported to be one of the paroxetine metabolites in humans. Thus, the piperidine derivative was converted to its N-tert-butoxycarbonyl (N-Boc) derivative, which was then converted to N-Boc paroxetine. Paroxetine hydrochloride propan-2-ol (isopropyl alcohol (IPA)) solvate crystals were directly obtained from the N-Boc paroxetine by adding hydrogen chloride to the N-Boc paroxetine IPA solution. The amount of IPA content in the crystals was reduced by drying with a continuous change of powder X-ray diffraction patterns. Other characterizations of the solvate crystals were also conducted.
