[(1R, 3S) -3-hydroxycyclopentyl] aminomethyl tert butyl ester (CAS: 225641-84-9): Research and application of a high-value chiral drug intermediate
In modern drug development, the synthesis and control of chiral molecules are one of the key factors determining drug efficacy and safety.
[(1R, 3S) -3-hydroxycyclopentyl] tert butyl carbamate (English name: * Carbomic acid, [(1R, 3S) -3-hydroxycyclopentyl] -1,1-diethylester *, CAS number: 225641-84-9) is a chiral compound with a clear structure and a single configuration, which has important application value in the fields of organic synthesis and medicinal chemistry.
This article will systematically introduce this Boc protected amino alcohol intermediate from its basic physicochemical properties, core applications, chiral characteristics, synthetic significance, and precautions.
English name :Carbamic acid, [(1R, 3S) -3-hydroxycyclopentyl] -1,1-diethylethyl ester (9CI)
Molecular formula :C10H19NO3
Molecular weight :201.26
CAS number :225641-84-9
Structural formula:
Structural features include Boc protecting group+(1R, 3S) -3-hydroxycyclopentane skeleton
This compound is a white or off white solid that is soluble in common organic solvents such as dichloromethane, methanol, DMF, etc. It is stable at room temperature and suitable for laboratory storage and use.
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Core use: The “key building block” for drug synthesis
1. Drug intermediates and active molecule precursors
The main function of this compound is as a pharmaceutical intermediate. The tert butoxycarbonyl (Boc) group in its structure is a classic amino protecting group that can stabilize the amino group in subsequent synthesis steps and avoid side reactions. Meanwhile, Boc groups can be easily removed under mild acidic conditions (such as TFA), facilitating the step-by-step construction of complex molecules.
For example, it can be used to synthesize small molecule inhibitors or candidate drugs targeting specific targets such as kinases, receptors, or proteases.
2. Precursor drug design
Research has shown that this compound can also serve as a structural unit for prodrugs. Hydroxyl and amino groups can be protected and deprotected, allowing for controlled release of active pharmaceutical ingredients in vivo or in vitro, thereby improving the pharmacokinetic properties of drugs.
3. Synthesis of Peptides and Peptide like Compounds
In peptide chemistry, [(1R, 3S) -3-hydroxycyclopentyl] amino acid tert butyl ester can be used as a conformational limiting amino acid analogue, introducing a cyclopentane skeleton to improve the metabolic stability and conformational rigidity of peptides, which is beneficial for designing highly selective peptide drugs.
Chiral Characteristics: The Value of (1R, 3S) Configuration
The chiral identifier of this compound is (1R, 3S), which belongs to a single enantiomer rather than a racemic mixture.
This is crucial because many biological targets, such as enzymes and receptors, only recognize molecules of specific configurations. Using a single configuration of intermediate can:
Reduce the production of ineffective or harmful enantiomers;
Improve the efficiency of synthetic routes;
Reduce the cost of subsequent splitting.
In contrast, the racemic form (CAS: 207729-03-1) may have significant differences in physicochemical properties and biological activity between the two.
Synthesis significance and research and development value
In the laboratory and process development stage, this compound is often used as:
1. Organic synthetic blocks: participate in the construction of complex natural product or drug skeletons;
2. Precursors of chiral catalysts or ligands: providing a chiral environment for asymmetric catalytic reactions;
3. Compound library construction: used for high-throughput screening to discover lead compounds.
Due to its clear structure, good stability, and easy operation, this compound has been widely used in academic research and early drug discovery.
Security and Storage Information
1. Attention: This compound is only for research and development in professional laboratories and should not be used for non research purposes such as medicine, food, or household use.
2. Storage conditions: sealed, dry, away from light, refrigerated at 2-8 ° C;
3. Safety: Avoid inhaling dust, wear gloves, goggles, and lab coats during operation;
4. Stability: Stable under normal storage conditions, avoid contact with strong acids and oxidants..
Frequently Asked Questions (FAQ)
1. Can this compound be used for human or pharmaceutical preparations?
No. This product is only used as a chemical intermediate in the research and development stage and has not undergone human safety evaluation. It cannot be directly used as a drug.
2. How to remove Boc protecting groups?
Usually, trifluoroacetic acid (TFA) is used to react at room temperature in dichloromethane, or an organic solution of hydrochloric acid (such as HCl/dioxane) can be used for smooth removal.
3.What is the difference between CAS: 207729-03-1 and CAS: 207729-03-1?
CAS: 207729-03-1 is the racemic form of the compound, containing two configurations: (1R, 3S) and (1S, 3R); CAS: 225641-84-9 is a single (1R, 3S) configuration with higher stereochemical purity.
Summary
[(1R, 3S) -3-hydroxycyclopentyl] aminomethyl tert butyl ester (CAS: 225641-84-9) is a structurally clear and widely used chiral drug intermediate. It combines Boc protecting groups with chiral cyclopentanol skeleton, and has important value in fields such as medicinal chemistry, peptide synthesis, and asymmetric catalysis.
With the increasing demand for chiral drugs, synthetic blocks with clear configurations, easy modification, and deprotection like this will play an increasingly critical role in new drug development.
Product Manager Email:ada@coreychem.com
