What Is tert-Butyl N-[(1R,2S,5S)-2-Amino-5-(dimethylcarbamoyl)cyclohexyl]carbamate Oxalate?

tert-Butyl N-[(1R,2S,5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl]carbamate oxalate (Aladdin SKU: T172592) is a chiral, polyfunctional cyclohexane derivative featuring three contiguous stereocenters (1R, 2S, 5S). The molecule carries three key functional groups: a tert-butoxycarbonyl (Boc)-protected secondary amine, a free primary amine stabilized as its oxalate salt, and an N,N-dimethylamide (dimethylcarbamoyl) substituent.

The oxalate salt form is commonly adopted to improve the stability and handling characteristics of the free amine, which can otherwise be hygroscopic or prone to degradation. This salt form also facilitates accurate weighing and long-term storage without significant loss of chemical integrity.

Because it presents two orthogonally addressable nitrogen functionalities and a well-defined three-dimensional scaffold, this compound serves as a versatile building block in medicinal chemistry and process chemistry for the assembly of complex target molecules.

Handling, Storage and Safety Considerations

Storage: Store the compound in a tightly sealed container in a cool, dry location away from direct light and sources of moisture. Specific temperature recommendations (e.g., refrigeration at 2–8 °C or ambient) should be confirmed by consulting the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) provided with the product, as conditions may vary by lot.

Handling: As with all fine chemicals containing reactive amine functionality, standard laboratory precautions apply: use appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a lab coat. Weigh the compound in a well-ventilated area or fume hood. The oxalate salt is an acid salt; avoid contact with strong bases or oxidizers.

Stability: The Boc group is acid-labile and will cleave under strongly acidic conditions (e.g., TFA or HCl in organic solvent). Avoid prolonged exposure to acidic environments during storage. The oxalate counterion is stable under normal storage conditions but should not be confused with the free base form when preparing stock solutions.

Disposal: Dispose of residues and solutions in accordance with local regulations governing organic chemical waste. Consult the SDS for hazard classification details.

Synthetic Applications and Use in Research

The combination of a Boc-protected amine and a free primary amine (as oxalate salt) on a rigid, stereodefined cyclohexane scaffold makes this compound a highly attractive intermediate for multi-step synthesis. Researchers can selectively deprotect the Boc group under mild acidic conditions to unmask the secondary amine, while the primary amine can be engaged in acylation, reductive amination, sulfonylation, or coupling reactions — either sequentially or in a differentiated one-pot strategy.

The dimethylcarbamoyl group introduces an amide bioisostere motif commonly exploited in medicinal chemistry to modulate solubility, metabolic stability, and target binding. Cyclohexane-based scaffolds with defined stereocenters are privileged structures in drug discovery, offering conformational rigidity that can translate into improved selectivity and potency at biological targets.

Typical applications include: (1) construction of kinase inhibitor scaffolds, (2) assembly of protease inhibitor pharmacophores, (3) synthesis of GPCR-targeted ligands, and (4) use as a chiral linker or amine fragment in DNA-encoded chemical library (DEL) synthesis. Users should optimize reaction conditions (solvent, base, temperature) for their specific coupling partners.

Purity, Quality and Analytical Specifications

Aladdin Scientific supplies T172592 with a purity specification confirmed by standard analytical techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. The Certificate of Analysis (CoA) accompanying each lot provides the specific purity value, appearance description, and analytical data for that batch.

Stereochemical integrity is a critical quality attribute for this compound. The defined 1R,2S,5S configuration should be confirmed by optical rotation measurement and/or chiral HPLC as reported on the CoA. Users who require independent verification of stereochemical purity are advised to perform chiral analytical methods in-house.

When preparing solutions, account for the oxalate salt form: the molecular weight used for molarity calculations must correspond to the salt (free base + oxalic acid), not the free base alone. Consult the product page or CoA for the exact molecular weight of the salt form. Solubility is typically best assessed empirically in the intended solvent system (e.g., DMSO, water, methanol) prior to large-scale use.

Ordering, Availability and Customer Support

tert-Butyl N-[(1R,2S,5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl]carbamate oxalate is available from Aladdin Scientific under catalog number T172592. To place an order, visit the Aladdin Scientific website, search for the catalog number or product name, select the required quantity and grade, and proceed through the standard checkout process.

For bulk quantities, custom synthesis inquiries, or requests for additional analytical data (e.g., chiral purity reports, additional NMR spectra), please contact Aladdin Scientific customer support directly via the contact details listed on the website. Lead times may vary depending on stock availability and order volume.

If you have technical questions about this product — including recommended reaction conditions, compatibility with specific reagents, or troubleshooting synthesis issues — our technical support team is available to assist. References to published literature using structurally similar building blocks may also be provided upon request, subject to availability.