Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate
[CAS# 851000-71-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate
• Synonyms: 1-Boc-3-phenyl-3-hydroxypyrrolidine
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.33
• CAS Registry Number: 851000-71-0
• EC Number: 978-633-5
• SMILES: CC(C)(C)OC(=O)N1CCC(C1)(C2=CC=CC=C2)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.555, Calc.^*
• Boiling Point: 386.7±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 187.7±27.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate is an organic compound that belongs to the pyrrolidine family, a class of nitrogen-containing heterocycles widely studied for their biological and chemical properties. This compound features a pyrrolidine ring attached to both a tert-butyl ester group and a phenyl group, with a hydroxyl group at the 3-position of the pyrrolidine ring. The molecular structure allows it to participate in a range of chemical reactions, making it a valuable intermediate in organic synthesis.

The discovery of tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate is tied to ongoing research in the field of asymmetric synthesis, where the introduction of functional groups such as hydroxyl, ester, and phenyl groups is essential for creating diverse molecules with specific properties. Pyrrolidine derivatives, in particular, are of significant interest because of their involvement in important natural products, pharmaceuticals, and materials. The development of such compounds often results from efforts to modify the pyrrolidine ring to enhance its stability, reactivity, or selectivity in chemical processes.

One key application of tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate lies in its use as a building block in the synthesis of complex molecules. The tert-butyl ester group enhances its solubility and stability, making it easier to handle and incorporate into synthetic pathways. The hydroxyl group provides opportunities for further functionalization, while the phenyl group contributes to the compound’s structural diversity. As an intermediate, it can be used to form larger molecules through processes such as esterification, reduction, or condensation reactions.

This compound also holds potential in medicinal chemistry. Pyrrolidine derivatives are often explored for their biological activities, such as antimicrobial, anti-inflammatory, and anticancer properties. The incorporation of both hydroxyl and phenyl groups in tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate could enhance its pharmacological activity or improve its bioavailability, making it a candidate for further investigation in drug design. The structural features of this compound may also allow it to interact with specific receptors or enzymes, potentially leading to the development of therapeutic agents targeting diseases such as cancer, Alzheimer’s, or diabetes.

In addition to its applications in synthetic chemistry and drug development, tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate can be utilized in the creation of chiral materials and catalysts. The presence of the chiral center in the pyrrolidine ring enables it to serve as a ligand or catalyst in asymmetric reactions, such as the asymmetric reduction of carbonyl compounds or the synthesis of optically active molecules. These reactions are crucial in the preparation of fine chemicals, pharmaceuticals, and agrochemicals, where the stereochemical purity of the final product is often a key factor in its efficacy and safety.

In conclusion, tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate is a versatile compound with broad applications in organic synthesis, medicinal chemistry, and materials science. Its ability to act as an intermediate in the synthesis of complex molecules, along with its potential pharmacological properties, makes it an important subject of study in both research and industrial settings. The further exploration of its reactivity and interactions could lead to the development of novel materials and therapeutic agents.