228244-20-0

Usage

Uses

Used in Organic Synthesis:
(R)-1-Boc-2-cyanopyrrolidine is used as a key intermediate in the synthesis of various organic compounds. Its unique structure and the presence of the Boc group make it a valuable building block for creating complex molecules with specific functionalities.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (R)-1-Boc-2-cyanopyrrolidine is employed as a precursor in the development of new drugs. Its versatility and stability contribute to the creation of potential therapeutic agents, with the Boc group playing a crucial role in protecting reactive sites during the synthesis process.
Used in Laboratory Research:
(R)-1-Boc-2-cyanopyrrolidine is utilized in academic and research settings for the investigation of chemical reactions and mechanisms. Its stereochemistry and the presence of the Boc group make it an interesting subject for studying the effects of structural modifications on reaction outcomes and the properties of synthesized compounds.

InChI:InChI=1/C10H16N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(12)7-11/h8H,4-6H2,1-3H3/t8-/m1/s1

Upstream product

• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 956285-06-6 tert-butyl (R)-2-((hydroxyimino)methyl)pyrrolidine-1-carboxylate 
• 73286-71-2 N-(tert-butoxycarbonyl)-2,3-dihydropyrrole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 344-25-2 D-Prolin 
• 70138-72-6 (R)-2-carbamoylpyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 956274-11-6 (R)-2-(2H-Tetrazol-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 739363-75-8 C₅H₈N₂ 
• 1266665-51-3 VPC₉₆₁₁₅ 
• 1266666-45-8 (R)-1-(4-dodecylbenzoyl)pyrrolidine-2-carbonitrile 

Relevant academic research and scientific papers

Evidence and exploitation of dicationic ammonium-nitrilium superelectrophiles: direct synthesis of unsaturated piperidinones

Exploiting superacid activation, the reactivity of aminonitriles was enhanced through the transient formation of highly reactive ammonium-nitrilium superelectrophiles. Demonstrated by usingin situlow-temperature NMR experiments and confirmed by X-ray diffraction analysis, these dications can be intramolecularly trapped by non-activated alkenes to generate unsaturated piperidinones, including enantioenriched ones, in a straightforward way.

Asymmetric Hydrocyanation of Alkenes without HCN

A general and efficient rhodium-catalyzed asymmetric cyanide-free hydrocyanation of alkenes has been developed. Based on the asymmetric hydroformylation/condensation/aza-Cope elimination sequences, a broad scope of substrates including mono-substituted, 1,2-, and 1,1-disubstituted alkenes (involving natural product R- and S-limonene) were employed, and a series of valuable chiral nitriles are prepared with high yields (up to 95 %) and enantioselectivities (up to 98 % ee). Notably, the critical factor to achieve high enantioseletivies is the addition of catalytic amount of benzoic acid. This novel methodology provides an efficient and concise synthetic route to the intermediate of vildagliptin and anagliptin.

METHOD FOR PRODUCING CHIRAL AMINONITRILES

The invention relates to a method for preparing an N-acyl- or N-sulfonyl-α-aminonitrile, comprising the following steps: a) condensation of an N-acyl- or N-sulfonyl-α-aminoaldehyde with hydroxylamine to give an aldoxime, and b) dehydration of the aldoxime

Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin

An alternative route toward enantiomerically highly enriched N-acyl amino nitriles based on the Cu(OAc)2-catalyzed dehydration of aldoximes, which are readily available from N-acyl l- or d-α-amino aldehydes through condensation with hydroxylamine, has been developed. The desired products were obtained with high conversion and in enantiomeric excesses of 97-99% ee. Furthermore, this method has been applied in the synthesis of an N-chloroacetylated 2-cyanopyrrolidine, which represents a building block for the synthesis of Vildagliptin.

One-pot oxidative conversion of alcohols into nitriles by using a TEMPO/PhI(OAc)2/NH4OAc system

A direct conversion of alcohols into nitriles with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO), iodosobenzene diacetate, and ammonium acetate as a nitrogen source is reported. This transformation, which proceeds through an oxidation-imination-aldimine oxidation sequence in situ, has been applied to a range of aliphatic, benzylic, heteroaromatic, allylic, and propargyl alcohols. Highly chemoselective ammoxidation of primary alcohols in the presence of secondary alcohols was also achieved. Georg Thieme Verlag Stuttgart New York.

IMIDAMIDE SPHINGOSINE KINASE INHIBITORS

Imidamide (amidine) analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 and SphK2) are provided. The compounds can prevent angiogenesis in tumors.

Development of amidine-based sphingosine kinase 1 nanomolar inhibitors and reduction of sphingosine 1-phosphate in human leukemia cells

Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.

The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids

Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

Constrained peptidomimetics reveal detailed geometric requirements of covalent prolyl oligopeptidase inhibitors

Prolyl oligopeptidases cleave peptides on the carboxy side of internal proline residues and their inhibition has potential in the treatment of human brain disorders. Using our docking program FITTED, we have designed a series of constrained covalent inhibitors, built from a series of bicyclic scaffolds, to study the optimal shape required for these small molecules. These structures bear nitrile functional groups that we predicted to covalently bind to the catalytic serine of the enzyme. Synthesis and biological assays using human brain-derived astrocytic cells and endothelial cells and human fibroblasts revealed that these compounds act as selective inhibitors of prolyl oligopeptidase activity compared to prolyl-dipeptidyl-aminopeptidase activity, are able to penetrate the cells and inhibit intracellular activities in intact living cells. This integrated computational and experimental study shed light on the binding mode of inhibitors in the enzyme active site and will guide the design of future drug-like molecules.

MGluR5 modulators I

The present invention is directed to novel compounds, to a process for their preparation, their use in therapy and pharmaceutical compositions comprising the novel compounds.