75773-76-1

Upstream product

• 116774-46-0 (S)-N-Benzylpyrrolidine-2-carboxyamide 
• 87766-32-3 (2S)-5-oxopyrrolidine-2-carboxylic acid benzylamide 
• 100-46-9 benzylamine 
• 511543-55-8 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione 
• 121611-64-1 (S)-benzyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylate 
• 98-79-3 L-Pyroglutamic acid 
• 147-85-3 L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 92235-33-1 (S)-tert-butyl 2-(benzylcarbamoyl)pyrrolidine-1-carboxylate 
• 3304-59-4 N-benzyloxycarbonyl-L-proline p-nitrophenyl ester 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Downstream Products

• 189107-17-3 (7aS,3S)-3-piperidino-1,2,5,6,7,7a-hexahydro-2-(phenylmethyl)pyrrolo<1,2-c><1,3,2>-diazaphosphole 3-oxide 
• 1188416-06-9 (S)-2-benzyltetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione 
• 1266229-67-7 benzyl {(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-phenylethyl}carbamate 
• 1266230-12-9 benzyl {(1S)-1-(4,4-difluorocyclohexyl)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxoethyl}carbamate 
• 1266230-03-8 benzyl [(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethyl]carbamate 
• 1266229-75-7 (3S,8aR)-2-[(2S)-2-amino-2-phenylacetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide 
• 1266230-13-0 (3S,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide 
• 1266229-74-6 tert-butyl [(1S)-2-({(1S)-2-[(3S,8aR)-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-phenylethyl}amino)-1-methyl-2-oxoethyl]methylcarbamate 
• 1266230-14-1 C₃₄H₄₉F₂N₅O₆ 
• 1266229-49-5 C₁₇H₂₄N₂O₂ 
• 1621189-26-1 (S)-2-benzyl-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-ium hexafluorophosphate 

Relevant academic research and scientific papers

Tetrahydropyrrole diamine-based bridged bisphenol rare earth metal complex as well as preparation method and application thereof

Ln Is a rare earth metal and a preparation method and an application thereof. R1 And R2 Is selected from tert-butyl, respectively. One of cumyl or triphenyl. The complex provided by the invention has the rare earth element and tetrahydropyrrole diamine base bridging ligand, can effectively catalyze ring opening reaction, and is high in reaction rate, high in activity and mild in reaction condition. The invention further provides a preparation method of the compound shown I. The invention also provides an application of the biodegradable high-molecular material polyhydroxybutyrate (PHB), the ring opening polymerization rate is improved, the preparation method is simpler and easier to control, the yield is high, and the cost is low.

Transfer hydrogenation reactions catalyzed by chiral half-sandwich Ruthenium complexes derived from Proline

Chiral ruthenium half-sandwich complexes were prepared using a chelating diamine made from proline with a phenyl, ethyl, or benzyl group, instead of hydrogen on one of the coordinating arms. Three of these complexes were obtained as single diastereoisomers and their configuration identified by X-ray crystallography. The complexes are recyclable catalysts for the reduction of ketones to chiral alcohols in water. A ruthenium hydride species is identified as the active species by NMR spectroscopy and isotopic labelling experiments. Maximum enantio-selectivity was attained when a phenyl group was directly attached to the primary amine on the diamine ligand derived from proline. [Figure not available: see fulltext.]

Asymmetric transfer hydrogenation reaction in water: Comparison of chiral proline amide/amine ruthenium(II) complexes

Chiral proline amide/amine ligands (2, 3), synthesized by multi-step reaction starting from l-proline (1), were evaluated as catalyst generated in situ from [RuCl2(p-cymene)]2 for asymmetric transfer hydrogenation of aromatic ketones in the presence of sodium formiate and sodium dodecyl sulfate (SDS). The results revealed that efficiencies and enantioselectivities strongly depend on the N-substituents.

Synthesis and characterization of new chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline

A short and flexible procedure for the preparation of seven chiral azolinium and five functionalized chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline has been developed. Moderate to good overall yields were obtained. Some NHC dimers and thiones were isolated. X-ray crystal structure determinations of two [Rh-NHC] complexes were also reported.

Design and synthesis of potent inhibitor of apoptosis (IAP) proteins antagonists bearing an octahydropyrrolo[1,2-a]pyrazine scaffold as a novel proline mimetic

To develop novel inhibitor of apoptosis (IAP) proteins antagonists, we designed a bicyclic octahydropyrrolo[1,2-a]pyrazine scaffold as a novel proline bioisostere. This design was based on the X-ray co-crystal structure of four N-terminal amino acid residues (AVPI) of the second mitochondria-derived activator of caspase (Smac) with the X-chromosome-linked IAP (XIAP) protein. Lead optimization of this scaffold to improve oral absorption yielded compound 45, which showed potent cellular IAP1 (cIAP1 IC50: 1.3 nM) and XIAP (IC50: 200 nM) inhibitory activity, in addition to potent tumor growth inhibitory activity (GI50: 1.8 nM) in MDA-MB-231 breast cancer cells. X-ray crystallographic analysis of compound 45 bound to XIAP and to cIAP1 was achieved, revealing the various key interactions that contribute to the higher cIAPI affinity of compound 45 over XIAP. Because of its potent IAP inhibitory activities, compound 45 (T-3256336) caused tumor regression in a MDA-MB-231 tumor xenograft model (T/C: -53% at 30 mg/kg).

Heterocyclic Compound

The present invention provides a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof. The compound of the present invention shows a strong IAP antagonistic activity.

The catalytic potential of 4-guanidinylpyridines in acylation reactions

A series of 3-alkyl-4-guanidinylpyridines with variable alkylation pattern have been synthesized and characterized with respect to their catalytic potential in acylation reactions of alcohols. The ability of the substitution pattern to stabilize acylpyridinium cations, which act as critical intermediates in the catalytic cycle of pyridine-catalyzed acylation reactions, has been assessed at the MP2(FC)/6-31+G(2d,p)//B98/6-31G(d) level of theory and inclusion of solvent effects in chloroform using the PCM continuum solvation model. The most active 4-guanidinylpyridines are among those having the most electron-rich pyridine ring. The influence of the type and concentration of the auxiliary base on the catalytic activity has also been studied. While the change from triethylamine to N,N-diisopropylethylamine as the auxiliary base does not lead to a systematic increase or decrease in the catalytic rates, the complete absence of auxiliary base leads to a 27-fold reduction in reaction rate. Georg Thieme Verlag Stuttgart.

A new chiral synthesis of Wieland-Miescher ketone catalyzed by a combination of (S)-N- benzyl-N(2-pyrrolidinylmethyl)amine derivative and bronsted acid

New or known N-benzyl-N (2-pyrrolidinylmethyl)amine derivatives bearing a variety of substituents on the aromatic ring were easily prepared from N-Boc-proline or NBoc-prolinol. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and Bronsted acid to prepare Wieland-Miescher ketone was examined in detail. During the examination, remarkable substitutional effects on the aromatic ring were observed. Development of a catalytic version of the reaction was successfully achieved by the use of N(9-anthracenyl)methyl-N(2-pyrrolidinyl-methyl)amine in the presence of dichloroacetic acid.

Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid

Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism

Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.