22795-99-9Relevant articles and documents
A (S)- l - ethyl -2 - aminomethylpentazane industrial manufacturing method (by machine translation)
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Paragraph 0073-0074; 0077, (2017/04/03)
The present invention provides a (S)- l - ethyl -2 - aminomethylpentazane industrial manufacturing method, characterized in that in order to 4 - hydroxy butyraldehyde as the substrate, under the action of in ethylamine generated by the reaction ring ortho-substituted 1 - ethyl pyrrolidine, after the reduction reaction to obtain the target product. In the present invention uses a novel, high-yield (S)- l - ethyl -2 - aminomethylpentazane method, the method is different from the traditional synthetic method, without complicated purification process, can be one-pot synthesis to realize, the process route avoids complex of problems and purification problems by-product. (by machine translation)
Exploring steric effects in diastereoselective synthesis of chiral aminophenolate zinc complexes and stereoselective ring-opening polymerization of rac-lactide
Wang, Haobing,Yang, Yang,Ma, Haiyan
, p. 7356 - 7372 (2016/08/06)
A series of tridentate chiral aminophenol proligands and corresponding zinc complexes, LZnX (L = (S)-2-{[(1-R4-2-pyrrolidinyl)CH2N(R3)-]CH2}-6-R1-4-R2-C6H2O, X = N(SiMe3)2, R3 = nBu, R4 = Bn: R1 = R2 = Cl (1), R1 = R2 = Me (2), R1 = R2 = tBu (3); X = N(SiMe3)2, R1 = trityl, R2 = Me: R3 = n-octyl, R4 = Bn (4), R3 = Bn, R4 = Bn (5), R3 = nBu, R4 = naphthalen-1-ylmethyl (6), R3 = nBu, R4 = iPr (7); R1 = R2 = cumyl, R3 = Et, R4 = Bn: X = N(SiMe3)2 (8), X = OtBu (9), X = Et (10), X = Cl (11)), have been synthesized. Complexes 4, 6, and 11 were obtained as enantiopure products (4 and 6 as enantiopure a; 11 as enantiopure b), while complexes 1-3, 5, and 7-10 as a pair of diastereomers, but in different ratios, which have been proved by X-ray diffraction and NMR spectroscopic studies. When exposed to the ring-opening polymerization of rac-lactide, most of these complexes can effectively produce PLAs with narrow polydispersities, desirable molecular weights, and moderate to high isotacticities. The structure-selectivity relationships, including the relationships of structure-synthesis diastereoselectivity and structure-polymerization stereoselectivity, have been further investigated. Consistent trends of diastereoselectivity and stereoselectivity are observed with the variations of the R1 group at the ortho-position of the phenolate ring and the R3 group in the pyrrolidinyl moiety. The decrease of the steric bulkiness of the R4 group on the central amine has less influence on the diastereoselectivity, but leads to considerable loss of the stereoselectivity, whereas the decrease of the steric bulkiness of the X group results in a reverse of the diastereoselectivity, but shows no influence on the stereoselectivity. There is probably no direct relationship between the diastereoselectivity in complex synthesis and the stereoselectivity of the complex toward the ROP of rac-LA. The stereocontrol of these complexes might largely rely on the substituents in the ligand framework rather than their diastereomer ratios.
Highly diastereoselective synthesis of chiral aminophenolate zinc complexes and isoselective polymerization of rac-lactide
Wang, Haobing,Ma, Haiyan
, p. 8686 - 8688 (2013/09/23)
An enantiopure zinc complex supported by an aminophenolate ligand with multiple stereogenic centers has been diastereoselectively synthesized via the variation of the ortho-substituent of a phenoxy moiety and the N-alkyl group of a chiral pyrrolidinyl ring in the ligand framework, which displays high isoselectivity in the polymerization of rac-lactide.
EFFICIENT STEREOCONSERVATIVE SYNTHESIS OF 1-SUBSTITUTED (S)- AND (R)-2-AMINOMETHYLPYRROLIDINES AND INTERMEDIATES THERETO
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, (2008/06/13)
Stereoconservative method for preparation of an (R)- or (S)-isomer of the compound of the formula I with at least 95% optical purity wherein R1 is a hydrogen atom, a saturated or unsaturated lower alkyl group, a cycloalkyl group, or a group (CH2)m Ph wherein m is 0-3 and Ph is a substituted or unsubstituted phenyl group including 1) O,N-dialkylation, directly or stepwise of (R)- or (S)-proline 2) aminolysis 3) reduction to formation of the (R)- or (S)-isomer of the compound of the formula I, and new intermediates II and III in optical active form obtained by the reaction steps above and wherein R2 is defined as R1 above.
Synthesis and in vitro evaluation of 2,3-dimethoxy-5-(fluoroalkyl)-substituted benzamides: High-affinity ligands for CNS dopamine D2 receptors
Bishop,Mathis,Gerdes,Whitney,Eaton,Mailman
, p. 1612 - 1624 (2007/10/02)
A number of 2,3-dimethoxy-5-(fluoroalkyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl] benzamides (with or without a 6-hydroxy group) were synthesized and evaluated as dopamine D2 receptor ligands. The parent acids were synthesized via the Claisen rearrangement of the appropriate O-allyl ethers, which were derived from o-vanillic acid or 2,3-dimethoxysalicylic acid. A decrease in reactivity was found to be characteristic of pentasubstituted benzoates, and difficulties were encountered with the introduction of fluorine onto the ethyl side chains. The (fluoroethyl)- and (fluoropropyl)salicylamides were 5 times more potent than the corresponding benzamides in inhibiting [3H]spiperone binding to the D2 receptor. These (fluoroalkyl)salicylamides are of potential value for in vivo positron emission tomography (PET) studies upon the basis of their relatively selective, high potency binding affinity for the D2 receptor.
Efficient Stereoconservative Syntheses of 1-Substituted (S)- and (R)-2-Aminomethylpyrrolidines
Hoegberg, Thomas,Raemsby, Sten,Stroem, Peter
, p. 660 - 664 (2007/10/02)
Three-step stereoconservative syntheses of chiral 1-substituted 2-aminomethylpyrrolidines with high optical purities from D- or L-proline are described.The key intermediates, 1-substituted prolinamides, were obtained by N,O-dialkylation of proline followed by ammonolysis or by 1-alkylation of prolinamide.Reduction furnished the optically pure (about 99percent e.e.) pyrrolidine derivatives, which are useful as intermediates in the preparation of antipsychotic substituted benzamides.
