53618-21-6Relevant articles and documents
Reductive Knoevenagel Condensation with the Zn-AcOH System
Ivanov, Konstantin L.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 1285 - 1291 (2020/11/13)
An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.
Synthesis of (±)-Pregabalin by Utilizing a Three-Step Sequential-Flow System with Heterogeneous Catalysts
Ishitani, Haruro,Kanai, Kan,Saito, Yuki,Tsubogo, Tetsu,Kobayashi, Shū
supporting information, p. 6491 - 6494 (2017/10/18)
(±)-Pregabalin, a γ-amino acid derivative, has been synthesized by utilizing flow methods. A three-step sequential-flow reaction starting from commercial isovaleraldehyde and methyl malonate proceeded smoothly with heterogeneous catalysts to afford the precursor of pregabalin in yields of 75–100 %, and a space-time yield of 52.2 g/L d was reached. In addition, a heterogeneous catalyst for the Knoevenagel reactions of aldehydes with malonates, which is the first step of the synthesis, has been developed. Pregabalin was finally obtained by acid-catalyzed hydrolysis of the precursor followed by neutralization.
PROCESS FOR PRODUCING OPTICALLY ACTIVE 4-NITRO-BUTANOIC ACID ESTER AND PREGABALIN
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Paragraph 0040, (2017/12/27)
PROBLEM TO BE SOLVED: To provide a process for producing optically active pregabalin with low number of reaction steps and low cost, as well as to provide a process for producing optically active 4-nitro-butanoic acid ester for use in said process. SOLUTION: Provided is a process for producing optically active 5-methyl-3-nitromethyl-2-alkoxycarbonyl-hexanoic acid alkyl ester by reacting dialkyl malonate and 4-methyl-1-nitro-1-pentene in the presence of a chiral catalyst containing a pyridine bisoxazoline derivative and calcium oxide; and a process for producing pregabalin using the present production process. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
β- and δ-amino acids (2,3- and 3,4-trans-CHA) as catalysts in Knoevenagel condensation and asymmetric aldol reactions
Al-Momani, Lo'Ay Ahmed,Lorbach, Volker,Detry, Jean,Geilenkirchen, Petra,Müller, Michael
supporting information, p. 172 - 183 (2018/05/09)
The efficacy of the β- and δ-amino acids (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-dienecarboxylic acid (2,3-trans-CHA) and (3R,4R)-4-amino-3-hydroxycyclohexa-1,5-dienecarboxylic acid (3,4-trans-CHA) as catalysts in Knoevenagel condensation and aldol additio
Hydroxy-L-prolines as asymmetric catalysts for aldol, Michael addition and Mannich reactions
Al-Momani, Lo'ay A.
experimental part, p. 101 - 111 (2012/05/20)
The hydroxyprolines (Hyps) 2-6 are tested as organocatalysts for aldol, Michael additions, and Mannich reactions. The results are compared with the well-known analogous L-proline (1).The effect of the additional hydroxyl group and chiral center was invest
PROCESSES FOR MAKING PREGABALIN AND INTERMEDIATES THEREFOR
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Page/Page column 8, (2009/12/27)
Processes for making a diester compound of formula (B) and for converting it to pregabalin, especially via a compound of formula (2), can provide several advantages. The compound (B) can be converted to the compound (2) via reductive hydrogenation.
Biosynthetic production of (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid (2,3-CHA)
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, (2008/06/13)
The invention relates to a process for the biosynthetic production and recovery of [5S,6S]-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid) catalyzed, at increased enzyme activity, at least by an enzyme belonging to the class of aminodeoxyisochoris
Carboxylic acid derivatives that inhibit the binding of integrins to their receptors
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Page 18; 36, (2010/11/30)
A method for the inhibition of the binding of α4β1 integrin to its receptors, for example VCAM-1 (vascular cell adhesion molecule-1) and fibronectin; compounds that inhibit this binding; pharmaceutically active compositions comprising such compounds; and to the use of such compounds either a above, or in formulations for the control or prevention of diseases states in which α4β1 is involved.
A straightforward method for the synthesis of alkylidene and arylidene malonates through proline-catalyzed Knoevenagel condensation
Cardillo, Giuliana,Fabbroni, Serena,Gentilucci, Luca,Gianotti, Massimo,Tolomeklli, Alessandra
, p. 1587 - 1594 (2007/10/03)
A straightforward method for the synthesis of alkylidene/arylidene malonates and arylidene cyanoacetates, utilizing proline as an alternative to traditional catalysts is presented. A large number of unsaturated esters was obtained from the Knoevenagel reaction under very mild conditions and utilizing cheap reagents.
Synthesis of substituted cyclopropylphosphonates by Michael Induced Ring Closure (MIRC) reactions
Stevens, Christian V.,Van Heecke, Gino,Barbero, Carmen,Patora, Krystyna,De Kimpe, Norbert,Verhé, Roland
, p. 1089 - 1092 (2007/10/03)
A variety of cyclopropylphosphonates were prepared in moderate to good yields by Michael Induced Ring Closure of trialkyl phosphites with the corresponding β-bromoalkylidene cyanoacetates and malonates.
