(8alpha,9S)-6'-Methoxycinchonan-9-amine Trihydrochloride TCI M3873

TCI M3873 is (8alpha,9S)-6'-Methoxycinchonan-9-amine Trihydrochloride, the trihydrochloride salt of an amino-functionalised cinchona alkaloid derivative more commonly known as 9-amino-9-deoxy-epiquinine. The compound is one of the most important organocatalysts in modern asymmetric chemistry. Its core structure is derived from quinine, the natural alkaloid bearing a methoxy-substituted quinoline ring and a basic quinuclidine ring, but the hydroxyl group at the nine position has been replaced by a primary amino group with inversion of configuration, so that the molecule operates through an activation mechanism entirely different from that of the parent quinine.

The property that makes this catalyst so highly valued is the ability of its primary amino group to form both enamines and iminium species with carbonyl compounds, combined with the presence of the basic quinuclidine nitrogen that allows it to perform bifunctional catalysis. These two active centres held within a single rigid chiral framework are what enable the catalyst to control the direction from which reactants approach and to deliver products with high enantiomeric excess. The trihydrochloride salt form is chosen because the free base of the cinchona amine tends to be unstable and difficult to weigh accurately, whereas the salt is a far more practical material to handle on the bench.

In Indonesian laboratories this class of organocatalyst is typically encountered in university and institutional research groups working on asymmetric synthesis, medicinal chemistry intermediates, and natural product methodology. It is used on small scale in method development and reaction screening, where researchers pair the catalyst with an acid co-catalyst and evaluate solvent, temperature, and loading. Because it is supplied as a well-defined crystalline salt from a recognised reagent brand, it fits readily into the reproducible workflows that graduate research and published methodology demand.

• Asymmetric conjugate addition reactions, where the primary amine forms an iminium intermediate with an enone and the rigid cinchona framework directs the incoming nucleophile to a single prochiral face.
• Enamine-mediated asymmetric alpha-functionalisation of aldehydes and ketones, in which the catalyst generates a chiral enamine that reacts with electrophiles under stereochemical control from the quinuclidine-bearing scaffold.
• Bifunctional organocatalysis research, where the simultaneous presence of a nucleophilic primary amine and a basic quinuclidine nitrogen allows one molecule to activate both reaction partners at once.
• Methodology development and catalyst screening studies, since the compound is a widely cited benchmark organocatalyst that lets research groups compare their own systems against established asymmetric transformations.
• Preparation of enantioenriched building blocks for medicinal chemistry, where the high enantiomeric excess achievable with this catalyst supports the synthesis of single-enantiomer intermediates for further elaboration.

• Chemical name: (8alpha,9S)-6'-Methoxycinchonan-9-amine Trihydrochloride, also known as 9-amino-9-deoxy-epiquinine trihydrochloride

Store the container tightly closed in a cool, dry place away from direct sunlight, moisture, and sources of heat, following the storage conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original tightly sealed bottle or transfer it to a clean, dry, chemically compatible amber glass container, and consider storage in a desiccator for reagents that will be weighed repeatedly. Handle the solid in a fume hood using gloves, safety glasses, and a laboratory coat, and avoid generating dust when transferring. Close the container promptly after weighing to limit exposure to atmospheric moisture, and dispose of residues and contaminated consumables through the laboratory's normal chemical waste channels.

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