760178-50-5Relevant articles and documents
Method for preparing 3-pyrroline based on improved activated zinc powder
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Paragraph 0035-0059, (2021/09/04)
The invention discloses a method for preparing 3-pyrroline based on improved activated zinc powder, and belongs to the technical field of medicines, wherein dimethyl sulfoxide is used as a solvent, aromatic carboxylic acid is used for activating zinc powder, active zinc powder is obtained after filtering, the active zinc powder reacts with hydrochloric acid to generate reactive hydrogen, and the reactive hydrogen is used for selectively hydrogenating pyrrole to generate 3-pyrroline. According to the invention, aromatic carboxylic acid used in the invention not only can remove zinc oxide on the surface of the zinc powder, but also can form a coordination compound with a spatial network structure with zinc, so that the safety of the activated zinc powder is enhanced, and the reaction activity of the zinc powder and the selectivity of a pyrrole selective hydrogenation reaction are effectively improved; through the dispersion effect of dimethyl sulfoxide on the zinc powder, the activation effect of the zinc powder is enhanced; and dimethyl sulfoxide complexed on the surface of active zinc in the process of selective hydrogenation of pyrrole can effectively capture hydrogen ions and transmit the hydrogen ions to zinc powder, so that the generation of reactive hydrogen is promoted, and the conversion rate of the reaction is improved.
Practical one-pot and large-scale synthesis of N-(tert-butyloxycarbonyl)-3- pyrroline
Rajesh, Tammana,Azeez, Shaik Abdul,Naresh, Erragunta,Madhusudhan, Gutta,Mukkanti, Kagga
experimental part, p. 638 - 640 (2010/04/22)
N-(tert-Butyloxycarbonyl)-3-pyrroline was prepared with high purity in large scale starting from cis-1,4-dichloro-2-butene via delepine reaction and subsequent cyclization in the presence of potassium carbonate followed by N-Boc protection in methanol.Judicious selection of base and solvent led to the use of a single solvent, i.e., methanol, for cyclization as well as for N-Boc protection to render the one-pot process from compound 2 more practical and greener than the stepwise version.
Heterocyclic lithium amides as chiral ligands for an enantioselective hydroxyalkylation with n-BuLi
Duguet, Nicolas,Petit, Sylvain M.,Marchand, Philippe,Harrison-Marchand, Anne,Maddaluno, Jacques
, p. 5397 - 5409 (2008/12/21)
(Chemical Equation Presented) Chiral heterocyclic structures based on 3-aminopyrrolidines (3APs), 3-aminotetrahydrothiophens (3ATTs), and 3-aminotetrahydrofurans (3ATFs) have been synthesized. The corresponding lithium amides have been evaluated as chiral ligands in the condensation of n-BuLi on o-tolualdehyde. The returned levels of induction were in the 46-80% ee range. The cheap and easily prepared 3ATFLi's turned out to be also the best ligands, giving access to the expected R or S alcohols in a same 80% level of induction at -78°C in THF. In all cases, the sense of induction depends on the absolute configuration of C8 on the 3-amino appendage. A general concept is proposed to rationalize the process of induction in the presence of organolithium species.