155251-70-0

Usage

Uses

Used in Pharmaceutical Development:
(S)-tert-Butyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate is used as a building block for the development of new pharmaceuticals due to its potential to be modified with specific functional groups that can influence its biological activity. Its complex structure and possible interactions with enzymes or receptors involved in neurotransmission or other physiological processes make it a valuable tool in creating novel drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-tert-Butyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate serves as an important intermediate compound. Its unique structure allows for further chemical reactions to create a variety of other complex molecules, contributing to the advancement of chemical research and the development of new materials.

Upstream product

• 123-75-1 pyrrolidine 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 1192-63-8 1-pyrrolidinecarbonyl chloride 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 344-25-2 D-Prolin 
• 883565-15-9 C₁₅H₂₅NO₅ 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 147-85-3 L-proline 
• 1314867-09-8 (S)-tert-butyl 2-(diallylcarbamoyl)pyrrolidine-1-carboxylate 
• 34619-03-9 tert-butyldicarbonate 

Relevant academic research and scientific papers

The chiral diamine mediated asymmetric Baylis-Hillman reaction

A chiral diamine, easily prepared from proline, is an effective, asymmetric organic catalyst for the Baylis-Hillman reaction of aldehydes and methyl vinyl ketone, affording adducts with enantio-selectivities up to 75%.

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.

An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors

A series of ionizable prolyl oligopeptidase inhibitors were developed through the introduction of a pyridyl group to the P3 position of the prolyl oligopeptidase inhibitor structure. The study was performed on previously developed prolyl oligopeptidase in

Double-chiral binaphthalene O-N-N tridentate ligand and preparation method thereof

The invention discloses a bis-chiral binaphthalene O-N-N tridentate ligand and a preparation method thereof. The ligand has the structural formula shown in formula (L). The preparation method comprises the following steps: (1) taking chiral 2 - methyl -2 - methoxy -binaphthalene as a raw material and replacing the reaction with an aromatic ring. As an alternative to the hydroxy protecting group, a brominated derivative (compound IV) is obtained by bromination. (2) Starting from protected chiral proline, a variety of diamine structures are obtained by conversion (Compound B). (3) Compound IV and Compound B are coupled in the presence of a catalyst in the presence of a catalyst to obtain a binaphthalene O-N-N tridentate ligand with bichirality. The ligand preparation method is simple in raw material, and has important significance for asymmetric organic synthesis.

Total Synthesis of Mycenarubin A, Sanguinolentaquinone and Mycenaflavin B and their Cytotoxic Activities

Here we report the first total synthesis of the fungal alkaloids mycenarubin A, sanguinolentaquinone and mycenaflavin B. The pyrroloquinoline alkaloid mycenarubin A was obtained in 10 steps (21 % total yield, 92 % ee) from the known key precursor 6,7-bis(benzyloxy)indole by an asymmetric alkylation and a biomimetic ring closure as the key steps. The indolo-6,7-quinone sanguinolentaquinone was obtained in eight steps (28 % total yield). Mycenaflavin B was also obtained in eight steps starting from the same key precursor (total yield 15 %) by a biomimetic ring closure and an acid-catalysed decarboxylation reaction as the key steps. The cytotoxic activities of mycenarubin A and mycenaflavin B were evaluated against mouse fibroblasts (L929) and human malignant melanoma cells (RPMI-7951).

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.

α-Aminoamides as ligands in Goldberg amidations

α-Aminoamides are shown to be useful as ligands in Goldberg amidations. A number of α-aminoamides are examined and the importance of substitution on the α-aminoamides is explored. Acetamide is focused on as the nucleophilic coupling partner due to its low cost, stability and convenience as a protecting group. The initial substrate scope for these catalysts is explored and includes electronically activated and deactivated aryl bromides, however o-substituted aryl bromides are problematic.

Easily removable olefin metathesis catalysts

A small family of olefin metathesis catalysts bearing a polar quaternary ammonium group is described. The presence of this group allows for efficient separation of ruthenium impurities after the reaction. Application of catalysts 9 and 11 leads to organic

Dicarboxylic acid azacycle L-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions

A series of dicarboxylic acid azacycle L-prolyl-pyrrolidine amides was synthesized, and their inhibitory activity against prolyl oligopeptidase (POP) from porcine brain was tested. Three different azacycles were tested at the position beyond P3 and six different dicarboxylic acids at the P3 position. L-Prolyl-pyrrolidine and L-prolyl-2(S)-cyanopyrrolidine were used at the P2-Pl positions. The IC50 values ranged from 0.39 to 19000 nM. The most potent inhibitor was the 3,3-dimethylglutaric acid azepane L-prolyl-2(S)- cyanopyrrolidine amide. Molecular docking (GOLD) was used to analyze binding interactions between different POP inhibitors of this type and the POP enzyme. The data set consisted of the novel inhibitors, inhibitors published previously by our group, and well-known reference compounds. The alignments were further analyzed using comparative molecular similarity indices analysis. The binding of the inhibitors was consistent at the P1-P3 positions. Beyond the P3 position, two different binding modes were found, one that favors lipophilic structures and one that favors nonhydrophobic structures.

Design of an organocatalyst for the enantioselective Diels-Alder reaction with α-acyloxyacroleins

We have realized the first enantioselective organocatalytic Diels-Alder reaction between α-substituted acroleins, such as α-acyloxyacroleins, and not only cyclic but also acyclic dienes. α-Acyloxyacroleins are useful as synthetic equivalents of α-haloacro