149716-79-0

Basic information

• Product Name: (S)-N-Boc-pyrrolidin-2-ylboronic acid
• Synonyms: (S)-N-Boc-pyrrolidin-2-ylboronic acid
• CAS NO: 149716-79-0
• Molecular Formula: C₉H₁₈BNO₄
• Molecular Weight: 215
• Mol File: 149716-79-0.mol

Chemical Properties

• Boiling Point: 349.226 °C at 760 mmHg
• Flash Point: 165.006 °C
• Appearance: /
• Density: 1.15
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-N-Boc-pyrrolidin-2-ylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Boc-pyrrolidin-2-ylboronic acid(149716-79-0)
• EPA Substance Registry System: (S)-N-Boc-pyrrolidin-2-ylboronic acid(149716-79-0)

Safety Data

• Hazardous Substances Data: 149716-79-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as a reagent for the synthesis of various organic compounds. Its ability to form stable covalent bonds with a wide range of substrates makes it a valuable tool in the development of new chemical entities and the modification of existing ones.
Used in Pharmaceutical Industry:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique chemical properties and reactivity allow for the creation of novel drug candidates with potential therapeutic applications.
Used in Material Science:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as a building block in the development of new materials with specific properties. Its versatility in forming covalent bonds can lead to the creation of advanced materials with applications in various industries, such as electronics, energy, and biotechnology.
Used in Suzuki-Miyaura Coupling Reactions:
(S)-N-Boc-pyrrolidin-2-ylboronic acid is used as a coupling partner in Suzuki-Miyaura coupling reactions, a widely used method for the formation of carbon-carbon bonds. This reaction is essential in the synthesis of complex organic molecules, including those found in pharmaceuticals and agrochemicals.

InChI:InChI=1S/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-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 7732-18-5 water 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 411226-02-3 bis(tetrahydropyrrole)boron bromide 
• 121-43-7 Trimethyl borate 

Relevant articles and documents

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.

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.

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.