Production Method 1

595547-18-5

895245-31-5

Reaction Conditions

1.1 Reagents: Lithium borohydride Solvents: Tetrahydrofuran ;  0 °C → rt; 3 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water

Reference

Unexpected novel binding mode of pyrrolidine-based aspartyl protease inhibitors: design, synthesis and crystal structure in complex with HIV protease

Specker, Edgar; Boettcher, Jark; Brass, Sascha; Heine, Andreas; Lilie, Hauke; et al, ChemMedChem, 2006, 1(1), 106-117

tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate Raw materials

• (3R,4R)-1-tert-butyl 3,4-diethyl pyrrolidine-1,3,4-tricarboxylate

tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate Preparation Products

• tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate (895245-31-5)

• 1. An atlas of endohedral Sc2S cluster fullerenes?
  Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. Fowler Phys. Chem. Chem. Phys., 2017,19, 419-425
• 2. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
• 3. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 4. 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
• 5. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877

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

Introduction to Tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate (CAS No. 895245-31-5)

Tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate, identified by its CAS number 895245-31-5, is a compound of significant interest in the field of chemical biology and pharmaceutical research. This compound belongs to a class of molecules that exhibit unique structural and functional properties, making it a valuable candidate for further exploration in drug development and biomolecular interactions.

The molecular structure of tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate features a pyrrolidine core substituted with hydroxymethyl groups at the 3 and 4 positions, and a tert-butyl group at the 1 position. This arrangement imparts specific steric and electronic characteristics to the molecule, which are crucial for its potential applications in medicinal chemistry. The presence of multiple hydroxymethyl groups suggests that this compound may participate in hydrogen bonding interactions, a feature that is often exploited in the design of bioactive molecules.

In recent years, there has been growing interest in the development of novel scaffolds for drug discovery. The pyrrolidine ring system is particularly noteworthy due to its prevalence in biologically active compounds. For instance, several FDA-approved drugs contain pyrrolidine moieties, highlighting their importance as pharmacophores. The tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate structure represents an innovative modification of this scaffold, potentially offering new opportunities for therapeutic intervention.

One of the most compelling aspects of tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate is its potential as a building block for more complex molecules. The hydroxymethyl groups can serve as points of attachment for other functional groups, enabling the synthesis of derivatives with tailored properties. This flexibility makes it an attractive candidate for library synthesis efforts aimed at identifying new lead compounds.

Recent studies have begun to explore the biological activity of related pyrrolidine derivatives. For example, modifications of the pyrrolidine ring have been shown to influence binding affinity and selectivity in target proteins. The tert-butyl group, in particular, can enhance metabolic stability and improve oral bioavailability, which are critical factors in drug development. The combination of these features makes tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate a promising candidate for further investigation.

The synthesis of this compound involves multi-step organic transformations that require careful optimization to ensure high yield and purity. Advanced synthetic techniques, such as transition metal-catalyzed cross-coupling reactions and asymmetric hydrogenation, may be employed to construct the desired framework efficiently. The development of robust synthetic routes is essential for enabling large-scale production and subsequent biological evaluation.

In addition to its synthetic appeal, tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate has potential applications in materials science and polymer chemistry. The hydroxymethyl groups can participate in polymerization reactions, leading to the formation of novel polymeric materials with unique properties. Such materials could find applications in coatings, adhesives, or even biodegradable polymers.

The compound's ability to engage in hydrogen bonding also makes it a candidate for use as a chiral auxiliary or ligand in catalytic systems. Chiral molecules are crucial in asymmetric synthesis, where they help direct reactions towards specific enantiomers. By incorporating tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate into catalytic protocols, researchers may achieve higher levels of enantioselectivity and improve overall reaction efficiency.

Evaluation of the pharmacological properties of tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate is ongoing and will require collaboration between synthetic chemists and biologists. Initial studies may focus on assessing its interaction with biological targets such as enzymes or receptors. Computational modeling techniques can also play a role in predicting binding affinities and understanding molecular recognition processes.

The long-term goal is to identify novel therapeutic agents based on this scaffold. By systematically modifying the structure and evaluating the biological activity of derivatives, researchers can uncover new mechanisms of action and develop treatments for unmet medical needs. The versatility of tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate makes it a valuable asset in this endeavor.

In conclusion, tert-butyl trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate (CAS No. 895245-31-5) represents a fascinating molecule with diverse potential applications. Its unique structural features make it an attractive candidate for drug discovery efforts aimed at developing new therapeutics. Furthermore，its utility extends to materials science and catalysis，underscoring its broad relevance across multiple scientific disciplines.

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