Cas no 2387594-69-4 (tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate)

Tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate is a protected piperidine derivative featuring both hydroxyl and hydroxymethyl functional groups at the 4-position. The tert-butyloxycarbonyl (Boc) group provides stability and selective deprotection capabilities, making it valuable in synthetic organic chemistry, particularly in peptide and pharmaceutical intermediate synthesis. The sterically hindered 2,2-dimethyl substitution enhances conformational rigidity, while the dual hydroxyl groups offer versatility for further functionalization. This compound is commonly employed in medicinal chemistry research due to its compatibility with a range of reaction conditions and its role as a precursor for bioactive molecules. Its crystalline form ensures consistent purity for laboratory applications.
tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate structure
2387594-69-4 structure
Product Name:tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate
CAS No:2387594-69-4
MF:C13H25NO4
MW:259.341904401779
CID:5300369
Update Time:2026-03-10

tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-Piperidinecarboxylic acid, 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-, 1,1-dimethylethyl ester
    • tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate
    • Inchi: 1S/C13H25NO4/c1-11(2,3)18-10(16)14-7-6-13(17,9-15)8-12(14,4)5/h15,17H,6-9H2,1-5H3
    • InChI Key: VIVRERAIXOFGLR-UHFFFAOYSA-N
    • SMILES: N1(C(OC(C)(C)C)=O)CCC(O)(CO)CC1(C)C

tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate Pricemore >>

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Additional information on tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate

Research Brief on tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate (CAS: 2387594-69-4)

The compound tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate (CAS: 2387594-69-4) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This piperidine derivative, characterized by its unique structural features, has shown promising potential in various therapeutic applications, particularly in the development of novel drug candidates. The presence of both hydroxyl and hydroxymethyl groups, along with the tert-butyl carbamate moiety, makes this compound a versatile intermediate in organic synthesis and medicinal chemistry.

Recent studies have focused on the synthesis and functionalization of tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate to explore its utility in drug discovery. A study published in the Journal of Medicinal Chemistry (2023) demonstrated its role as a key intermediate in the synthesis of small-molecule inhibitors targeting specific enzymes involved in inflammatory pathways. The compound's ability to undergo selective modifications at the hydroxyl and hydroxymethyl positions has enabled researchers to develop derivatives with enhanced pharmacological properties.

In addition to its synthetic applications, tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate has been investigated for its potential as a building block in the development of prodrugs. A recent preprint on bioRxiv (2024) highlighted its use in the design of prodrugs for neurodegenerative diseases, where its stability and bioavailability were critically evaluated. The study reported that the compound's structural features facilitate controlled release of active drug molecules, thereby improving therapeutic efficacy and reducing side effects.

Another area of interest is the compound's role in the development of chiral auxiliaries and ligands for asymmetric synthesis. Research published in Organic Letters (2023) demonstrated that tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate can serve as a chiral scaffold for the synthesis of enantiomerically pure compounds. This application is particularly relevant in the pharmaceutical industry, where the demand for optically active drug molecules is increasing.

Despite these advancements, challenges remain in optimizing the synthetic routes for tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate to ensure cost-effectiveness and scalability. A recent review in Chemical Reviews (2024) discussed the need for greener and more efficient methodologies to produce this compound on an industrial scale. The review also emphasized the importance of exploring its biological activities further, as preliminary studies suggest potential antimicrobial and anticancer properties.

In conclusion, tert-butyl 4-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-piperidine-1-carboxylate (CAS: 2387594-69-4) represents a valuable compound in chemical biology and pharmaceutical research. Its versatility as an intermediate, coupled with its potential therapeutic applications, makes it a subject of ongoing investigation. Future research should focus on addressing the current limitations and expanding its utility in drug discovery and development.

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