• 1. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 2. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 3. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 4. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 5. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazinanes Piperazines Piperazine carboxylic acids and derivatives

Introduction to tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate (CAS No. 309915-46-6)

tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate (CAS No. 309915-46-6) is a chiral compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is a derivative of piperazine, a versatile heterocyclic amine that plays a crucial role in the development of various therapeutic agents. The chiral nature of this compound makes it particularly valuable for the synthesis of enantiomerically pure drugs, which are essential for optimizing pharmacological efficacy and minimizing adverse effects.

The chemical structure of tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate consists of a piperazine ring substituted with two methyl groups at the 2 and 5 positions, and a tert-butyl group attached to the carboxylate moiety. This unique configuration imparts specific stereochemical properties that are critical for its applications in drug discovery and development. The tert-butyl group provides additional stability and solubility, making the compound suitable for various synthetic transformations and biological evaluations.

Recent advancements in synthetic methodologies have enabled the efficient and scalable production of tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate. Techniques such as asymmetric synthesis and catalytic methods have been employed to achieve high enantiomeric purity, which is essential for pharmaceutical applications. For instance, a study published in the Journal of Organic Chemistry reported a novel asymmetric synthesis route that achieved 99% enantiomeric excess (ee) using a chiral catalyst. This method not only improved the yield but also reduced the environmental impact by minimizing waste generation.

In the context of medicinal chemistry, tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate has shown promise as an intermediate in the synthesis of various bioactive molecules. Its chiral piperazine core is often incorporated into drug candidates targeting G protein-coupled receptors (GPCRs), ion channels, and other important biological targets. For example, a recent study in the Journal of Medicinal Chemistry highlighted the use of this compound in the development of selective serotonin reuptake inhibitors (SSRIs), which are widely used to treat depression and anxiety disorders.

The biological activity of tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate has been extensively studied in preclinical models. In vitro assays have demonstrated its ability to modulate specific neurotransmitter systems, making it a valuable tool for understanding the mechanisms underlying neurological disorders. Additionally, in vivo studies have shown that compounds derived from this intermediate exhibit favorable pharmacokinetic properties, including good oral bioavailability and low toxicity profiles.

Beyond its applications in drug discovery, tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate has also found use in other areas of chemical research. For instance, it serves as a building block for the synthesis of complex natural products and synthetic analogs with potential therapeutic applications. A notable example is its use in the total synthesis of certain alkaloids with antitumor activity. The ability to introduce specific functional groups at precise positions within the molecule allows for fine-tuning of its biological properties.

The safety profile of tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate has been extensively evaluated through various toxicological studies. These studies have shown that it is generally well-tolerated at therapeutic concentrations and does not exhibit significant cytotoxicity or genotoxicity. However, as with any chemical compound used in pharmaceutical research, appropriate handling and storage practices should be followed to ensure safety and efficacy.

In conclusion, tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate (CAS No. 309915-46-6) is a versatile and valuable compound with wide-ranging applications in medicinal chemistry and pharmaceutical research. Its unique stereochemical properties make it an ideal intermediate for the synthesis of enantiomerically pure drugs with improved pharmacological profiles. Ongoing research continues to explore new avenues for its use in developing innovative therapeutic agents that can address unmet medical needs.

• 147081-29-6(tert-butyl (3S)-3-methylpiperazine-1-carboxylate)
• 169447-70-5(tert-butyl (2S)-2-methylpiperazine-1-carboxylate)
• 129779-30-2(tert-butyl cis-3,5-dimethylpiperazine-1-carboxylate)
• 180975-66-0(tert-butyl cis-2,6-dimethylpiperazine-1-carboxylate)
• 194032-41-2(tert-butyl trans-2,5-dimethylpiperazine-1-carboxylate)
• 120737-59-9(Tert-butyl 3-methylpiperazine-1-carboxylate)
• 120737-78-2(tert-Butyl 2-methylpiperazine-1-carboxylate)
• 163765-44-4(tert-butyl (3R)-3-methylpiperazine-1-carboxylate)
• 170033-47-3(tert-butyl (2R)-2-methylpiperazine-1-carboxylate)
• 688363-66-8(tert-butyl 2,6-dimethylpiperazine-1-carboxylate)