149682-75-7

Basic information

• Product Name: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester
• Synonyms: (+/-)-1-(TERT-BUTOXYCARBONYL)PYRROLIDINE-2-BORONIC ACID;1-N-Boc-pyrrolidin-2-ylboronic acid;1-(Tert-butoxycarbonyl)pyrrolidin-2-ylboronic acid;1-(tert-butoxycarbonyl)pyrrolidin-2-yl-2-boronic acid;(N-(1,1-diMethylethoxycarbonyl)pyrrolidin-2-yl)boronic acid;N-Boc-pyrrolidin-2-yl]boronic Acid;1-pyrrolidinecarboxylic acid 2-broMo-1-(1,1-diMethylethyl)ester;1-N-Boc-pyrrolidin-2-ylboronic acid, 95+%
• CAS NO: 149682-75-7
• Molecular Formula: C₉H₁₈BNO₄
• Molecular Weight: 215.05452
• Product Categories: Chiral Compounds
• Mol File: 149682-75-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 349.226 °C at 760 mmHg
• Flash Point: 165.006 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 2.89E-06mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly)
• PKA: 9.94±0.20(Predicted)
• CAS DataBase Reference: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester(149682-75-7)
• EPA Substance Registry System: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester(149682-75-7)

Safety Data

• Hazardous Substances Data: 149682-75-7(Hazardous Substances Data)

Usage

Description

2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester, commonly known as Boc-protected proline boronic acid, is a white solid compound with unique chemical properties. It is a derivative of proline, an essential amino acid, and features a boronic acid group that allows for versatile chemical reactions. The Boc-protecting group ensures the stability of the cyclic amine during synthesis processes, making it a valuable intermediate in the preparation of various heterocyclic boronic acid compounds.

Uses

Used in Pharmaceutical Industry:
2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester is used as a key intermediate in the synthesis of heterocyclic boronic acid compounds for pharmaceutical applications. Its unique structure allows for the development of novel drugs with potential therapeutic benefits, particularly in the treatment of various diseases and disorders.
Used in Chemical Research:
In the field of chemical research, 2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester serves as a valuable building block for the creation of complex organic molecules. Its reactivity and stability make it an ideal candidate for exploring new chemical reactions and developing innovative synthetic pathways.
Used in Material Science:
The unique properties of 2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester also make it a promising candidate for the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of advanced materials with improved characteristics, such as enhanced stability, reactivity, or selectivity.

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

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 121-43-7 Trimethyl borate 
• 1333-74-0 hydrogen 
• 135884-31-0 N-boc-2-pyrroleboronic acid 
• 7732-18-5 water 

Downstream Products

• 138371-54-7 (±)-tert-butyl 2-(3-phenylpropanoyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

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.

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.

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.