cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole: Properties & Applications
cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole: Properties & Applications
cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole is a saturated bicyclic nitrogen-containing heterocycle that serves as a versatile chiral scaffold in medicinal chemistry and the synthesis of pharmacologically active compounds.
- Product Name
- cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole
- SKU
- C733817
- Compound Class
- Bicyclic saturated pyrrolopyrrole (pyrrolidine-fused heterocycle)
- Sterochemistry
- cis configuration at the ring fusion centers
- Primary Application
- Synthetic building block in medicinal chemistry and drug discovery
- Nitrogen Atoms
- Two secondary/tertiary amine nitrogens within the bicyclic framework
Chemical Structure and Stereochemistry
cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole consists of two fused five-membered pyrrolidine rings sharing a common bond, forming a compact bicyclic scaffold. The cis designation refers to the relative stereochemistry at the two ring-fusion carbon centers, with substituents oriented on the same face of the bicyclic ring system. One nitrogen bears the N-methyl substituent, while the second nitrogen retains a secondary amine character, providing a handle for further functionalization.
This rigid, three-dimensional architecture is particularly valuable in drug design, as it constrains the spatial presentation of pharmacophoric groups, potentially improving selectivity and binding affinity toward biological targets compared with flexible acyclic analogs.
Physicochemical Properties
As a fully saturated bicyclic amine, cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole exhibits physicochemical properties typical of sp³-rich nitrogen heterocycles. The compound is expected to display basic character due to the presence of two amine nitrogens, rendering it amenable to salt formation with organic and inorganic acids — a property exploited during purification and formulation of active pharmaceutical ingredients.
Its relatively low molecular weight and high fraction of sp³ carbons (Fsp³) align with modern medicinal chemistry guidelines that correlate increased Fsp³ with improved aqueous solubility, reduced promiscuity, and better clinical success rates. Researchers are advised to consult the certificate of analysis (CoA) supplied with SKU C733817 for confirmed purity data and any available spectroscopic characterization.
Synthetic Utility and Applications in Drug Discovery
The cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole scaffold has attracted attention as a privileged structure in medicinal chemistry. Its secondary amine nitrogen serves as a nucleophilic site for acylation, sulfonylation, reductive amination, and transition-metal-catalyzed cross-coupling reactions, enabling rapid generation of diverse analog libraries.
Bicyclic pyrrolidine motifs related to this scaffold appear in the literature as pharmacophores targeting a range of biological receptors and enzymes. The enforced cis ring fusion pre-organizes the molecule into a defined three-dimensional shape, which can be exploited to achieve complementary shape matching with enzyme active sites or receptor binding pockets. This makes C733817 a useful intermediate for structure–activity relationship (SAR) studies in early-stage drug discovery programs.
Handling, Storage, and Safety Considerations
Like most reactive amine-containing building blocks, cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole should be handled with standard laboratory precautions. Users are advised to wear appropriate personal protective equipment (PPE), including gloves, safety glasses, and a lab coat, and to work in a well-ventilated fume hood to minimize inhalation exposure.
The compound should be stored under conditions specified on the product label and CoA — typically in a tightly sealed container away from moisture, heat, and incompatible oxidizing agents. For long-term storage, refrigeration or freezing may be recommended to maintain integrity and purity. Always refer to the Safety Data Sheet (SDS) available from Aladdin Scientific for detailed hazard classifications, first-aid measures, and disposal guidance.
Frequently asked questions
What is cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole used for?
It is primarily used as a synthetic building block in medicinal chemistry and drug discovery. Its bicyclic pyrrolidine scaffold and secondary amine functionality allow diverse chemical transformations, making it valuable for generating compound libraries in SAR studies.
What does the cis configuration mean for this compound?
The cis configuration refers to the relative orientation of hydrogen atoms (or substituents) at the two ring-fusion stereocenters, both residing on the same face of the bicyclic ring system. This enforced geometry imparts a defined three-dimensional shape to the molecule, which is important for achieving selective interactions with biological targets.
How should cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole (C733817) be stored?
The compound should be stored sealed, away from moisture and heat, following the conditions stated on the product label and Certificate of Analysis. For extended storage, refrigerated or frozen conditions may be advisable. Always consult the Aladdin Scientific SDS for full storage and safety guidance.
What types of chemical reactions can be performed on this scaffold?
The secondary amine nitrogen in cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole can undergo acylation, sulfonylation, reductive amination, and various transition-metal-catalyzed coupling reactions. These transformations enable rapid diversification of the core scaffold for medicinal chemistry applications.
References
- Aladdin Scientific product page and Certificate of Analysis for cis-1-Methylhexahydropyrrolo[3,4-b]pyrrole, SKU C733817.
- Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009, 52, 6752–6756. doi:10.1021/jm901241e
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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