tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate
[CAS# 365998-36-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate
• Molecular Formula: C₁₄H₂₇N₃O₃
• Molecular Weight: 285.38
• CAS Registry Number: 365998-36-3
• EC Number: 877-156-9
• SMILES: CC(C)(C)OC(=O)N[C@@H]1C[C@H](CC[C@@H]1N)C(=O)N(C)C

Properties

• Solubility: Soluble (46 g/L) (25 °C), Calc.^*
• Density: 1.09±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.508, Calc.^*
• Boiling Point: 434.4±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 216.5±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate is a chemical compound that is widely studied in the field of organic chemistry for its potential applications in drug development and synthesis. This compound contains a cyclohexyl ring with three important functional groups: an amino group, a carbamate group, and a dimethylamino-carbonyl group. The stereochemistry of the molecule, indicated by the specific configurations at the 1R, 2S, and 5S positions, plays a crucial role in its reactivity and biological activity.

The discovery of this compound can be attributed to efforts aimed at exploring new amino acid derivatives with potential medicinal properties. The cyclohexane structure is of particular interest because it can be easily functionalized to introduce various bioactive groups, making it a versatile building block in medicinal chemistry. The amino group at position 2 is a common feature in many biologically active compounds, allowing for further modification and incorporation into therapeutic agents. The dimethylamino-carbonyl group at position 5 serves as a protecting group for the amine, which can be deprotected to expose the functional amine group for subsequent reactions.

Synthesis of tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate typically involves a multistep process. One common synthetic route involves starting with a commercially available cyclohexane derivative and introducing the amino group through nucleophilic substitution reactions. The dimethylamino-carbonyl group is then introduced by reacting the amine with dimethylcarbamoyl chloride in the presence of a base. The carbamate group is introduced by reaction with tert-butyl isocyanate, which serves as both the source of the carbamate group and the protecting group for the amine. Throughout the synthesis, careful control of reaction conditions is essential to maintain the desired stereochemistry and to avoid the formation of unwanted byproducts.

The primary application of this compound lies in its potential as a key intermediate in the synthesis of pharmaceutical agents. The functional groups present in the molecule allow for the development of drugs that can interact with specific biological targets. For example, the amino group can serve as a point of attachment for further functionalization, while the carbamate group can be used to modulate the compound’s solubility and stability. Additionally, the dimethylamino-carbonyl group can influence the compound's ability to cross biological membranes, a crucial factor in drug design. This compound is a promising candidate for the development of therapeutics aimed at treating diseases related to the nervous system, such as neurodegenerative disorders or psychiatric conditions, due to its potential ability to interact with receptors in the brain.

In addition to its role in drug synthesis, tert-butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate may also have applications in material science. The functionalized cyclohexane core can be incorporated into polymers or other materials, potentially altering the material's physical properties such as mechanical strength, flexibility, or chemical stability. As research continues, this compound could also be explored for its role in the development of new catalysts or in chemical reactions that require the specific reactivity of amino or carbamate groups.

In conclusion, tert-butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate is an important compound in the fields of organic and medicinal chemistry. Its unique structure, with multiple functional groups, makes it a versatile building block for the synthesis of bioactive molecules. Further studies on its synthesis and biological activity may lead to the development of novel therapeutic agents and advanced materials.

References

2019. Synthesis of an Edoxaban Fragment. Synfacts, 15(08).
DOI: 10.1055/s-0039-1690462

2014. Edoxaban. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0127