(+/-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehyde is a heterocyclic building block built around a five-membered pyrrolidine ring in which the ring nitrogen is already protected by a tert-butoxycarbonyl (Boc) group, while an aldehyde group is attached at the third position. The combination of these two functional groups makes it a highly useful synthetic intermediate in organic chemistry and medicinal chemistry laboratories. Its primary role is to supply a saturated cyclic amine framework that is ready to be extended or modified through its carbonyl group, while the ring nitrogen remains "locked" so that it does not participate in reactions and interfere with the synthetic route the researcher is designing.
The characteristic that makes this material a frequent choice lies in the compatibility of its two functional groups. The aldehyde group is electrophilic and readily directed into a range of classical transformations such as reductive amination, Wittig and Horner-Wadsworth-Emmons reactions, addition of organometallic reagents, aldol condensation, and oxidation to the corresponding carboxylic acid. The Boc group, meanwhile, is orthogonal to many basic and nucleophilic conditions, yet can be removed cleanly under acidic conditions to liberate the free secondary amine when the synthetic sequence calls for it. This pairing allows chemists to plan multi-step routes with predictable protection and deprotection points.
In Indonesian laboratories, this compound is typically used in university research groups, pharmaceutical and medicinal chemistry laboratories, and contract research settings that build small-molecule libraries. It is generally handled on a small scale at the bench, weighed under controlled conditions, and carried directly into coupling or chain-extension steps. Because the saturated nitrogen heterocycle motif appears often in drug discovery scaffolds, this building block supports both academic method development and applied compound synthesis programmes.
- Reductive amination: the free aldehyde reacts with primary or secondary amines to form an imine that is reduced in situ, giving substituted aminomethyl pyrrolidines without disturbing the Boc-protected ring nitrogen.
- Wittig and Horner-Wadsworth-Emmons olefination: the carbonyl group serves as the electrophilic partner for phosphorus ylides and phosphonate carbanions, allowing controlled carbon chain extension and introduction of alkene functionality.
- Organometallic addition: Grignard and organolithium reagents add across the aldehyde to produce secondary alcohols, giving a straightforward route to branched substituents on the pyrrolidine three-position.
- Aldol condensation and related carbonyl chemistry: the aldehyde participates in classical enolate chemistry, letting researchers assemble more complex carbon frameworks from a compact, readily available heterocyclic starting point.
- Medicinal chemistry scaffold preparation: after acidic Boc removal the resulting secondary amine can be acylated, alkylated, or coupled further, which suits the iterative construction of small-molecule libraries for screening.
| Brand | TCI |
|---|---|
| CAS number | 59379-02-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Heterocyclic Building Blocks |
| Pack sizes | available in standard TCI research-scale packaging; please confirm the pack size when ordering |
| Physical form | — |
| Storage | keep the container tightly closed and follow the storage conditions stated on the manufacturer's label and safety data sheet |
- Product code: B6091
Store the material in its original tightly closed container, in a cool, dry, and well-ventilated place away from direct sunlight, heat sources, and incompatible chemicals, following the conditions stated on the manufacturer's label and safety data sheet. Amber glass or the supplied original packaging is suitable, and containers should be resealed promptly after each use to limit exposure to air and moisture, since aldehydes are susceptible to oxidation. Handle in a fume hood using safety glasses, gloves, and a laboratory coat, avoid inhalation of vapours and contact with skin or eyes, and allow refrigerated material to reach room temperature before opening to prevent condensation. Dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.
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