149716-78-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(R)-N-Boc-pyrrolidin-2-ylboronic acid is used as a building block for the synthesis of various pharmaceutical and agrochemical compounds. Its versatility in organic synthesis allows for the creation of a wide range of molecules with potential therapeutic and pesticidal properties.
Used in Organic Synthesis:
(R)-N-Boc-pyrrolidin-2-ylboronic acid is used as a reagent in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for the formation of carbon-carbon bonds. Its ability to act as a ligand in palladium-catalyzed cross-coupling reactions further enhances its utility in organic synthesis, enabling the formation of complex molecular structures.
Used in Drug Development:
Due to its unique structural features and functional properties, (R)-N-Boc-pyrrolidin-2-ylboronic acid is used as a starting material in the development of novel drugs and biologically active molecules. Its potential applications in medicinal chemistry include the synthesis of compounds with targeted therapeutic effects and improved pharmacokinetic properties.

InChI:InChI=1/C9H18BNO4/c1-9(2,3)15-8(12)11-6-4-5-7(11)10(13)14/h7,13-14H,4-6H2,1-3H3/t7-/m0/s1

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 
• 135884-31-0 N-boc-2-pyrroleboronic acid 
• 1333-74-0 hydrogen 
• 28049-80-1 bis(diisopropylamino)chloroborane 
• 1310-73-2 sodium hydroxide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 411226-02-3 bis(tetrahydropyrrole)boron bromide 

Relevant academic research and scientific papers

A General C(sp3)-C(sp3) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids

A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp3-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.

Proline boric acid compound and preparation method and applications thereof

The invention provides a compound whose structure is shown as a formula (I) or a salt thereof. The compound is a proline boric acid proteasome inhibitor compound, and has good proteasome inhibitory activity and excellent druggability. The structural formula of the compound is shown as the formula (I).

Preparing technology of chiral N-BOC-pyrrolidine-2-boric acid

The invention discloses a preparing technology of chiral N-BOC-pyrrolidine-2-boric acid, and belongs to the field of agent intermediate synthesis. N-BOC-pyrrolidine and sec-butyllithium are subjectedto proton abstraction at low temperature, halogen boron agent is added, after a reaction is completed, saturated ammonium chloride is added to conduct cancellation, after evaporation to dryness of anorganic layer, mandelic acid and ethyl acetate are added, and after salt resolution, acidic hydrolysis is conducted to obtain chiral N-BOC-pyrrolidine-2-boric acid. By means of the method, the operating steps are short, raw materials are easily recycled, products with two structures can be obtained simply by changing the structure of a resolving agent, and the preparing technology has potential practical value.

Total synthesis of tetracyclic kynurenic acid analogues isolated from chestnut honey

A short and efficient synthesis of novel tetracyclic Kynurenic acid analogues, isolated from chestnut honey, is described. The crucial step of the strategy was a MW-assisted cyclization of enamines of ethyl dioxohexahydropyrrolizine and 2,3-dioxooctahydroindolizine carboxylates to obtain 2,3,6,11b-tetrahydro-1H-pyrrolizino[2,1-b]quinoline-5,11-dione and 5,8,91,011,11a-hexahydroindolizino[2,1-b]quinoline-6,12-dione, respectively. Because of its modular nature, the synthetic strategy can have value as a general method for the preparation of compounds containing these new heterocyclic scaffolds.

Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors

On the basis of the application of proline-boronic acid as pharmacophore in the kinase inhibitors and our previous research results, using proline-boronic acid as warhead, two series of peptide proline-boronic acids, dipeptide proline-boronic acids (I) and tripeptide proline-boronic acids (II), were designed and synthesized. All the synthesized compounds were first evaluated for their biological activity against MGC803 cell, and then, the best compound II-7 was selected to test its anti-tumor spectrum on six human tumor cell lines and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors.

METHODS FOR PREPARING DPP-IV INHIBITOR COMPOUNDS

Methods for preparing an inhibitor of dipeptidyl peptidase IV, as well as formulations of such inhibitors of dipeptidyl peptidase IV that have a high degree of stability including under warm, humid storage conditions.

A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties

(Chemical Equation Presented) A two-step, direct asymmetric synthesis of the trifluoroacetate ammonium salt of boroproline is reported. (-)-Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded N-Boc-aminoboronic acid in good yield and enantioselectivity as determined by HPLC (pinanediol ester). Deprotection using TFA yielded the ammonium salt; full characterization data are presented, and the structure in aqueous solution and the occurrence of a B-N species are discussed.

FIBROBLAST ACTIVATION PROTEIN INHIBITOR COMPOUNDS AND METHODS

Amino terminus-blocked peptide boronate compounds of Formulas I and II are useful for inhibiting Fibroblast Activation Protein (FAP) and other proteases, and for treating disorders mediated by FAP. Methods of using the amino terminus blocked peptide boronate compounds, and stereoisomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

HETEROCYCLIC BORONIC ACID COMPOUNDS

Dipeptidyl peptidase IV (DPP-IV)-inhibiting compounds are provided that have formula I: wherein n is 1 to 3; X is CH2; S; O; CF2 or C (CH3)2; Z is H; halogen; hydroxyl; (C1-6)alkoxy; (C1-12)alkyl; (C3-12)cycloalkyl; phenyl; or heteroaryl; where the phenyl and heteroaryl groups are optionally mono- or independently plurisubstituted with R7; optionally, X together with an adjacent ring carbon and Z form a fused cyclopropyl; and optionally, one of the bonds in the ring containing X is a double bond; and CriRii, R1, R1, R3, R4 and R5 are as described herein. Methods for preparing these compounds, and methods for treating diabetes, especially Type II diabetes, and other related diseases are described using the compounds of formula I in pharmaceutical compositions which contain these compounds. Pharmaceutical compositions which contain combinations of these compounds with other antidiabetic agents are also described herein.

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid: Efficient recycling of the costly chiral auxiliary (+)-pinanediol

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid (1) is detailed. A previously disclosed synthesis of 1 (Snow, R.; Kelly, T. R.; Adams, J.; Coutts, S.; Perry, C. (Boehringer Ingelheim Pharmaceuticals, Inc.). WO 93/10127, 1993) was significantly improved by developing an efficient process for recycling the costly chiral auxiliary (+)- pinanediol.