60419-23-0

Usage

Uses

Used in Biochemical Research:
(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine is used as a ligand or catalyst in biochemical research for its unique chiral structure and ability to interact with other molecules in specific ways. This property makes it valuable in the development of new chemical reactions and processes.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine is utilized as a chiral building block for the synthesis of pharmaceutical compounds. Its unique configuration allows for the creation of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects.
Used in Chiral Synthesis:
(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine is employed as a chiral auxiliary in asymmetric synthesis, aiding in the production of enantiomerically enriched compounds. This application is crucial in the development of new drugs with improved efficacy and selectivity.
Used in Analytical Chemistry:
This chiral compound is also used in analytical chemistry for the separation and analysis of enantiomers. Its unique properties can be leveraged to develop chiral stationary phases for chromatographic techniques, enabling the resolution of racemic mixtures into their individual enantiomers.

InChI:InChI=1/C9H18N2/c1-2-7-11(6-1)8-9-4-3-5-10-9/h9-10H,1-8H2/p+2/t9-/m1/s1

Upstream product

• 144243-45-8 (R)-(+)-1-prolinamidopyrrolidine 
• 147-85-3 L-proline 
• 68832-13-3 D-prolinol 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 128510-88-3 tert-butyl (R)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate 
• 344-25-2 D-Prolin 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 1192-63-8 1-pyrrolidinecarbonyl chloride 
• 4042-36-8 D-pyrrolidone-5-carboxylic acid 
• 110958-18-4 (R)-5-[(pyrrolidin-1-yl)carbonyl]pyrrolidin-2-one 
• 144243-44-7 tert-butyl (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate 
• 144243-44-7 (R)-(+)-1-pyrrolidine 

Downstream Products

• 575467-47-9 (E)-1-((R)-2-Pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-3-(4-trifluoromethyl-phenyl)-propenone 
• 477575-56-7 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-[3,5-dimethyl-4-((R)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one 
• 914298-88-7 (R)-(5-chloro-2,4-bis(methoxymethoxy)phenyl)(2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl)methanone 
• 1331786-35-6 (R)-(4-(5-(2-fluorobenzyloxy)-6-aminopyridin-3-yl)phenyl)-(2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl)methanone 
• 756520-43-1 (R)-(4-(5-benzyloxy-6-aminopyridin-3-yl)phenyl)(2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl)methanone 
• 756520-44-2 (R)-(4-(6-amino-5-hydroxypyridin-3-yl)phenyl)(2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl)methanone 
• 1227075-57-1 (R)-(2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone 

Relevant academic research and scientific papers

NOVEL BETULINIC SUBSTITUTED AMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to novel betulinic substituted amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and are Formula (II) as defined herein. The invention novel betulinic substituted amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

Enantioselective Synthesis of 6,6-Disubstituted Pentafulvenes Containing a Chiral Pendant Hydroxy Group

Simple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl function of a 1,2-formylacetophenone, followed by cyclization of a resulting fulvene-stabilized carbanion with the formyl group, generates bicyclic chiral alcohols with initial er values up to 94:6. Exceptional enantio-enrichment of the resultant alcohols results upon crystallization—even near racemic samples spontaneously de-racemize. This enables new families of substituted cyclopentadienes that are both enantiomerically and diastereomerically pure to be rapidly attained.

AMINOHETEROARYL COMPOUNDS AS PROTEIN KINASE INHIBITORS

Aminopyridine and aminopyrazine compounds of formula (1), compositions including these compounds, and methods of their use are provided. Preferred compounds of formula 1 have activity as protein kinase inhibitors, including as inhibitors of c-MET.

Sulfonamide lactam inhibitors of FXa and method

Sulfonamide lactams of the following formula wherein X, R1, R2, R3, R4, R4a, R5, R5a, R6, R6a, R7 and R8 are as described herein, are provided which inhibitors of Factor Xa and are useful as anticoagulants in the treatment of cardiovascular diseases associated with thromboses.

5-ARALKYSUFONYL-3-(PYRROL-2-YLMETHYLIDENE)-2-INDOLINONE DERIVATIVES AS KINASE INHIBITORS

The present invention relates to certain 5-aralkylsulfonyl-3-(pyrrol-2-yl-methylidene)-2-indolinone derivatives that inhibit kinases, in particular met kinase. Pharmaceutical compositions comprising these compounds, methods of treating diseases mediated by kinases utilizing pharmaceutical compositions comprising these compounds, and methods of preparing them are also disclosed.

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.

Asymmetric synthesis of N-substituted (R)-2-[(pyrrolidin-1-yl)methyl]pyrrolidines

The preparation of (R)-2[(pyrrolidin-1-yl)methyl] pyrrolidine and (R)-1-methyl-2-[(pyrrolidin-1-yl)methyl]pyrrolidine (both in 85% ee) is reported. The key step in the synthesis involves the sparteine-mediated asymmetric functionalization of N-Boc pyrrolidine and subsequent trapping with 1-pyrrolidine-carbonyl chloride.

Synthesis and Biological Evaluation of Conformationally Restricted 2-(1-Pyrrolidinyl)-N--N-methylethylenediamines as ? Receptor Ligands. 1. Pyrrolidine, Piperidine, Homopiperidine, and Tetrahydroisoquinoline Classes

The synthesis and ? receptor affinity of a series of conformationally restricted derivatives of 2-(1-pyrrolidinyl)-N--N-methylethylenediamine (1) is described.The pyrrolidinyl (or N,N-dialkyl), ethylenediamine, N-alkyl, and phenylethyl portions of this ? receptor pharmacophore were restricted by its incorporation into 1,2-cyclohexanediamine-, pyrrolidine-, piperidine-, homopiperidine-, and tetrahydroisoquinoline-containing ligands.The ? receptor binding affinities of these compounds were determined using (+)-pentazocine in guinea pig brain homogenates.The synthesis of all but one class was achieved by acylation and alane reduction of the appropriate diamine precursors whose synthesis is also reported. ? receptor affinities ranged from 1.34 nM for 6,7-dichloro-2-tetrahydroisoquinoline (12) to 455 nM for (1R,2R)-trans-N--N-methyl-2-(1-pyrrolidinyl)cyclohexylamine .In this displacement assay, (+)-pentazocine exhibited a Ki of 3.1 nM while DTG and haloperidol showed Ki values of 27.7 and 3.7 nM, respectively.The conformationally free parent compound 1 exhibited a Ki value of 2.1 nM.Comparison of both the ? receptor affinities and nitrogen atom geometry of the compounds revealed that a gauche relation of the nitrogen atoms of cis-1,2-cyclohexanediamines is not imperative for high affinity as we had previously thought.It is highly likely that nitrogen lone pair orientations and steric factors on the aliphatic portions of these ligands play a major role in the ? receptor binding of this pharmacophore.