(R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester
[CAS# 438631-77-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester
• Synonyms: 1-O-tert-butyl 3-O-methyl (3R)-piperazine-1,3-dicarboxylate
• Molecular Formula: C₁₁H₂₀N₂O₄
• Molecular Weight: 244.29
• CAS Registry Number: 438631-77-7
• EC Number: 823-090-0
• SMILES: CC(C)(C)OC(=O)N1CCN[C@H](C1)C(=O)OC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.472, Calc.^*
• Boiling Point: 321.3±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 148.1±26.5 °C, Calc.^*

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester is a significant chemical compound often used in the synthesis of biologically active molecules. This compound is a piperazine derivative with a Boc (tert-butoxycarbonyl) protective group attached to the nitrogen atom of the piperazine ring, which provides stability during synthetic reactions. The methyl ester group attached to the carboxylic acid residue further enhances the compound's reactivity, making it a useful intermediate in organic synthesis, particularly in the production of pharmaceuticals and other bioactive compounds.

The discovery of (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester is linked to the growing interest in piperazine derivatives in medicinal chemistry. Piperazine is a versatile heterocyclic compound widely used in drug design due to its ability to interact with a variety of biological targets. The introduction of functional groups, such as the Boc protection group and the ester, enhances the chemical properties of piperazine, making it more suitable for specific applications in drug discovery and development.

The synthesis of (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester typically involves the selective protection of the piperazine nitrogen using Boc anhydride, followed by esterification of the carboxyl group with methyl alcohol in the presence of an acid catalyst. This method allows for the creation of a stable intermediate, which can be further modified to produce a variety of derivatives. The use of the Boc group protects the piperazine nitrogen from unwanted reactions during synthesis, allowing for more selective functionalization of the molecule.

In terms of applications, (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester serves as a key intermediate in the synthesis of piperazine-based drugs. The compound is often used in the development of molecules targeting central nervous system disorders, such as anxiety and depression. Piperazine derivatives have been shown to exhibit activity against a range of receptors and enzymes involved in neurotransmission, making them valuable candidates for the design of new therapeutic agents. Furthermore, the ability to modify the functional groups attached to the piperazine ring allows for the development of compounds with improved pharmacokinetic properties, such as increased bioavailability and better tissue penetration.

Additionally, (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester is employed in the synthesis of peptide-based drugs. The piperazine ring structure can be incorporated into peptide sequences to enhance stability and facilitate drug delivery. The Boc group is especially useful in solid-phase peptide synthesis, where it protects the amine group during the synthesis process and can be removed under mild conditions to reveal the free amine for further reactions.

In conclusion, (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester is an important compound in organic and medicinal chemistry. Its role as an intermediate in the synthesis of piperazine-based drugs and its application in peptide synthesis have made it a valuable tool in drug discovery. Through the modification of its functional groups, (R)-1-N-Boc-piperazine-3-carboxylic acid methyl ester has enabled the development of more potent and selective therapeutic agents.

References

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