69500-64-7

Usage

Uses

Used in Asymmetric Synthesis:
(S)-(+)-2-(Aminomethyl)pyrrolidine is used as an organocatalyst for the asymmetric transformation of (S)-alanine. It plays a crucial role in enhancing the selectivity and efficiency of the reaction, leading to the formation of enantiomerically pure products.
Used in Asymmetric α-Fluorination:
In the field of organic chemistry, (S)-(+)-2-(Aminomethyl)pyrrolidine is used as a catalyst in the asymmetric α-fluorination of linear and branched aldehydes. The use of N-fluorobenzenesulfonamide as the fluorinating agent allows for the selective introduction of fluorine atoms, which can significantly impact the reactivity and properties of the resulting molecules.
Used in Schiff Base Metal Complexes:
(S)-(+)-2-(Aminomethyl)pyrrolidine is also used as a reactant to prepare Schiff base metal complexes with a pyrrolidine fragment as a ligand in asymmetric synthesis. These complexes are valuable in various applications, including catalysis and the development of new materials with unique properties.

InChI:InChI=1/C5H12N2/c6-4-5-2-1-3-7-5/h5,7H,1-4,6H2/t5-/m0/s1

Upstream product

• 96948-23-1 1-[(2S)-N-Benzylpyrrolidin-2-yl]methanamine 
• 204387-53-1 (2S)-pyrrolidine-2-carbonitrile 
• 119020-01-8 (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 62937-45-5 (R)-prolinamide 
• 259537-92-3 tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate 
• 62937-47-7 (2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 344-25-2 D-Prolin 
• 6404-31-5 Z-D-proline 
• 782495-18-5 N-(((2S,4R)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl)methyl)-1,1,1-trifluoromethanesulfonamide 
• 69610-41-9 Boc-L-Pro-H 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 34079-31-7 Z-Pro-NH₂ 
• 147-85-3 L-proline 

Downstream Products

• 1309561-99-6 (4aR,13aS)-N-[(2,4-difluorophenyl)methyl]-9,11-dioxo-10-[(phenylmethyl)oxy]-2,3,4a,5,9,11,13,13a-octahydro-1H-pyrido[1,2-a]pyrrolo[1',2':3,4]imidazo[1,2-d]pyrazine-8-carboxamide 
• 1206881-84-6 (S)-N-((1-(diphenylphosphoryl)pyrrolidin-2-yl)methyl)-P,P-diphenylphosphinic amide 
• 956468-16-9 N-[((2R)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-2-pyrrolidinyl)methyl]-3,4-bis(methyloxy)benzenesulfonamide 
• 956468-15-8 N-[((2S)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-2-pyrrolidinyl)methyl]-3,4-bis(methyloxy)benzenesulfonamide 
• 947150-28-9 (R)-hexahydropyrrolo[1,2-c]imidazol-3-one 
• 614753-12-7 4-[5,6-dichloro-1-(4-{[(pyrrolidin-2-ylmethyl)-amino]-methyl}-benzyl)-1H-benzoimidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester 
• 82935-51-1 (S)-2-<(3-bromo-2,6-dimethoxybenzamido)methyl>pyrrolidine 
• 110715-43-0 (3S,7aS)-3-anilino-1,2,5,6,7,7a-hexahydropyrrolo<1,2-c><1,3,2>diazaphosphole 3-oxide 
• 110638-60-3 3-anilino-1,2,5,6,7,7a-hexahydropyrrolo<1,2-c><1,3,2>diazaphosphole 3-oxide 
• 956467-82-6 N-[((2R)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-2-pyrrolidinyl)methyl]-3,4-bis(methyloxy)benzenesulfonamide 
• 956467-79-1 N-[((2S)-1-{[3,4-bis(methyloxy)phenyl]sulfonyl}-2-pyrrolidinyl)methyl]-N-methyl-3,4-bis(methyloxy)benzenesulfonamide 

Relevant academic research and scientific papers

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

D -Prolyl-2-(trifluoromethylsulfonamidopropyl)pyrrolidine: An Organocatalyst for Asymmetric Michael Addition of Aldehydes to β-Nitroalkenes at Ambient Conditions

Four 2-(trifluoromethylsulfonamidoalkyl)pyrrolidines and their d-prolinamides were prepared and screened as organocatalysts for the Michael addition reaction of aldehydes with β-nitroalkenes at rt and without the use of additives. d-Prolyl-2-(trifluoromet

Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes

An efficient method for the synthesis of 1,2-diamines from aldehydes through proline-catalyzed asymmetric α-amination followed by reductive amination is reported. The products resemble those obtained through direct asymmetric diamination of terminal alkenes. The methodology is used to synthesize 2-aminomethyl and 3-amino pyrrolidines and piperidines in high yields and with a good enantioselectivity. The usefulness of the method is demonstrated through the synthesis of a 2-aminomethyl iminocyclitol.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Biomimetic asymmetric Michael addition reactions in water catalyzed by amino-containing β-cyclodextrin derivatives

Nine β-cyclodextrin derivatives containing an amino group were synthesized via nucleophilic substitution from mono(6-O-p-tolylsulfonyl)-β-cyclodextrin and used in asymmetric biomimetic Michael addition reactions in water at room temperature. The mechanism responsible for the moderate activity and enantioselectivity of the β-cyclodextrin derivatives was explored using nuclear magnetic resonance spectroscopy, namely 2D 1H rotating-frame overhauser effect spectroscopy (ROESY), ultraviolet absorption spectroscopy, and quantum chemical calculations, which provide a useful technique for investigating the formation of inclusion complexes. The effects of the pH of the reaction medium, the β-cyclodextrin derivative dosage, the structure of the modifying amino group, and various substrates on the yield and enantioselectivity were investigated. The results indicated that these factors had an important effect on the enantiomeric excess (ee) in the reaction system. Experiments using a competitor for inclusion complex formation showed that a hydrophobic cavity is necessary for enantioselective Michael addition. A comparison of the reactions using 4-nitro-β-nitrostyrene and 2-nitro-β-nitrostyrene showed that steric hindrance improved the enantioselectivity. This was verified by the optimized geometries obtained from quantum chemical calculations. An ee of 71% was obtained in the asymmetric Michael addition of cyclohexanone and 2-nitro-β-nitrostyrene, using (S)-2-aminomethylpyrrolidine-modified β-CD as the catalyst, in an aqueous buffer solution, i.e., CH3COONa-HCl (pH 7.5).

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.]

Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to β-cyclodextrin in water

Two proline derivatives, (S)-2-aminomethylpyrrolidine and (R)-2-aminomethylpyrrolidine modified β-CD (CD-1, CD-2) were synthesized in the yields of 31% and 14%. Their self-inclusion conformations were characterized by 1H ROESY NMR studies and q

Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N-dimethyl-2(R)-aminomethylpyrrolidine)

A series of platinum(II) complexes were synthesised based on the enantiomerically pure amino acid proline. Novel synthetic pathways were developed, adapted from standard peptide chemistry, to produce the 2-aminomethylpyrrolidine (pyrr) ligand and its derivatives with differing arrangements of methyl substituents at the exocyclic amine sites. The crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N,N-dimethyl-2(R)-aminomethylpyrrolidine) is reported and the five-membered ligand ring has been shown to be in an envelope conformation. Cytotoxicity studies were carried out on the ovarian cancer A2780 tumour cell line and its cisplatin-resistant variant, A2780cisR. Remarkably good activity was seen for several of the drugs when compared to cisplatin despite the addition of substantial steric bulk to the amine groups, and there was a lack of cross-resistance with cisplatin seen for some compounds.

CHEMICAL COMPOUNDS

The present invention relates generally to novel therapeutic compounds and AXOR 109 agonists, and processes for the manufacture and use of the same.

POLYCYCLIC CARBAMOYLPYRIDONE DERIVATIVE HAVING HIV INTEGRASE INHIBITORY ACTIVITY

The present invention is to provide a novel compound (I), having the anti-virus activity, particularly the HIV integrase inhibitory activity, and a drug containing the same, particularly an anti-HIV drug, as well as a process and an intermediate thereof. Compound (I) wherein Z1 is NR4; R1 is hydrogen or lower alkyl; X is a single bond, a hetero atom group selected from O, S, SO, SO2 and NH, or lower alkylene or lower alkenylene in which the hetero atom group may intervene; R2 is optionally substituted aryl; R3 is hydrogen, a halogen, hydroxy, optionally substituted lower alkyl etc; and R4 and Z2 part taken together forms a ring, to form a polycyclic compound, including e.g., a tricyclic or tetracyclic compound.