Production Method 1

24424-99-5

92197-46-1

885277-59-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  4 h, 60 psi, 40 °C

Reference

An improved and scalable process for 3,8-diazabicyclo[3.2.1]octane analogues

Huang, Long-Jiang; Teng, Da-Wei, Chinese Chemical Letters, 2011, 22(5), 523-526

tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate Raw materials

• Di-tert-butyl dicarbonate
• (1-Benzylpyrrolidine-2,5-diyl)dimethanol

tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate Preparation Products

• tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate (885277-59-8)

• 1. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 2. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 3. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 4. An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins?
  Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois Mathey Dalton Trans., 2019,48, 5523-5526
• 5. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolidines Pyrrolidine carboxylic acids and derivatives Pyrrolidine carboxylic acids

Comprehensive Overview of tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate (CAS No. 885277-59-8)

The compound tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate (CAS No. 885277-59-8) is a highly versatile intermediate in organic synthesis and pharmaceutical research. Its unique structure, featuring a pyrrolidine core with dual hydroxymethyl groups and a tert-butyl carboxylate protecting group, makes it invaluable for constructing complex molecules. Researchers and industries are increasingly interested in this compound due to its applications in drug discovery, peptide synthesis, and materials science.

One of the key reasons for the growing popularity of tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate is its role in the development of bioactive molecules. The presence of two hydroxymethyl groups allows for further functionalization, enabling the creation of derivatives with tailored properties. This flexibility is particularly valuable in the design of small-molecule inhibitors and protease substrates, which are critical in modern therapeutic research.

In recent years, the demand for pyrrolidine-based compounds has surged, driven by their prevalence in FDA-approved drugs and natural products. CAS No. 885277-59-8 is often discussed in forums and scientific literature as a building block for chiral auxiliaries and ligands in asymmetric catalysis. Its stability under various reaction conditions further enhances its utility in multi-step synthetic routes.

Another area where tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate shines is in peptide mimetics. The pyrrolidine ring mimics proline-like structures, making it a valuable scaffold for designing peptidomimetics that resist enzymatic degradation. This property is especially relevant in the development of therapeutic peptides, a hot topic in biopharmaceutical research.

From an industrial perspective, scalability and purity are critical factors for CAS No. 885277-59-8. Manufacturers emphasize high-yield synthesis protocols to meet the needs of large-scale production. Analytical techniques such as HPLC and NMR are routinely employed to ensure the compound meets stringent quality standards, particularly for pharmaceutical applications.

Environmental and regulatory considerations also play a role in the adoption of tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate. Unlike some traditional reagents, this compound is often favored for its relatively benign environmental profile, aligning with the principles of green chemistry. Researchers are exploring its use in sustainable synthetic pathways to minimize waste and energy consumption.

Looking ahead, the applications of CAS No. 885277-59-8 are expected to expand further. Innovations in catalysis and bioconjugation techniques may unlock new roles for this compound in cutting-edge fields like targeted drug delivery and biomaterials. As the scientific community continues to explore its potential, tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate is poised to remain a cornerstone of synthetic chemistry.

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