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
• Article Data: 3

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

General Description

(S)-N-Boc-pyrrolidin-2-ylboronic acid is a specialized chemical compound often used in research and laboratory applications, particularly in the field of organic chemistry. Its systematic name is (2S)-2-(tert-Butoxycarbonyl)pyrrolidin-2-ylboronic acid. It belongs to the group of organic boronic acids, which are notable for their ability to form stable covalent bonds with diverse substrates and are commonly used in various synthesis processes like Suzuki-Miyaura coupling reactions. (S)-N-Boc-pyrrolidin-2-ylboronic acid is a chiral boronic acid, meaning it exists in different forms that are mirror images of each other. Its stereochemistry is indicated by the (S) prefix in its name.

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 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.