tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate: Key FAQs
tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate: Key FAQs
tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate is a versatile, Boc-protected pyrrolidine building block bearing a tosylate leaving group that enables efficient nucleophilic substitution reactions in the synthesis of complex amine-containing molecules.
- Product Name
- tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate
- SKU
- T729717
- Functional Groups
- Boc-protected secondary amine, tosylate (OTs) leaving group
- Core Structure
- Pyrrolidine ring with exocyclic methylene tosylate at C-3 position
- Primary Application
- Nucleophilic substitution and cross-coupling reactions in medicinal and synthetic chemistry
- Supplier
- Aladdin Scientific
What Is tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate?
tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate (SKU: T729717) is a pyrrolidine-based synthetic building block in which the ring nitrogen is protected as a tert-butyl carbamate (Boc group) and a tosylate (p-toluenesulfonate, OTs) ester is installed on the exocyclic methylene at the C-3 position. The Boc group provides orthogonal, acid-labile protection of the secondary amine, while the tosylate serves as an excellent leaving group for SN2 nucleophilic substitution, Mitsunobu-type reactions, and related transformations. The compound is widely used in medicinal chemistry as a chiral or racemic scaffold for the preparation of pyrrolidine-containing pharmacophores.
Key Chemical Properties and Storage
The tosylate leaving group makes this compound reactive toward a broad range of nucleophiles, including amines, thiols, alkoxides, azides, and organometallic reagents, under mild to moderate conditions. The Boc protecting group is stable under basic and neutral aqueous conditions but is readily cleaved by dilute strong acids such as trifluoroacetic acid (TFA) or hydrochloric acid in organic solvents. To maintain reagent integrity, the compound should be stored in a cool, dry environment, away from moisture and strong acids. Typical storage conditions for similar Boc-protected sulfonates are 2–8 °C or at room temperature under inert atmosphere; consult the product datasheet for confirmed specifications.
Note: Specific physicochemical data (MW, mp, purity grade) are not provided in the current source material; refer to the Aladdin Scientific product page or Certificate of Analysis for confirmed values.
Typical Synthetic Applications
This building block is particularly valuable in multi-step synthesis of nitrogen heterocycle-containing drug candidates and natural product analogues. Common transformations include: (1) displacement of the tosylate with carbon, nitrogen, oxygen, or sulfur nucleophiles to elaborate the C-3 side chain; (2) Boc deprotection followed by ring closure or further functionalization of the released amine; and (3) use as a precursor to chiral pyrrolidine methanol derivatives after selective reduction or hydrolysis steps. The combination of orthogonal protecting-group chemistry and a highly reactive leaving group in a single molecule streamlines the synthesis of structurally diverse pyrrolidine libraries for drug discovery.
Ordering and Availability from Aladdin Scientific
tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate is available from Aladdin Scientific under SKU T729717. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and add the desired quantity to your cart. For bulk quantities, custom packaging, or pricing inquiries, contact the Aladdin Scientific sales team directly. The product datasheet, Safety Data Sheet (SDS), and Certificate of Analysis (CoA) can be downloaded from the product page prior to purchase.
Frequently asked questions
What nucleophiles are compatible with the tosylate group in this compound?
The tosylate leaving group is compatible with a wide range of nucleophiles under Sₙ₂ conditions, including primary and secondary amines, sodium azide, thiols, alkoxides, and stabilized carbanions. Reactions are typically performed in polar aprotic solvents such as DMF or acetonitrile at room temperature to mild heating. Care should be taken to avoid strongly basic or nucleophilic conditions that might also cleave the Boc group.
How should the Boc group be removed after the desired substitution is complete?
The Boc protecting group is most commonly removed using trifluoroacetic acid (TFA, typically 20–50% v/v) in dichloromethane at room temperature for 30–60 minutes, or using 4 M HCl in dioxane. These conditions cleanly liberate the free secondary amine as its TFA or HCl salt. The reaction is highly selective and does not affect most other common functional groups under these mild acidic conditions.
Is this compound available as a single enantiomer or as a racemate?
The source material does not explicitly specify the stereochemical form available under SKU T729717. The compound possesses a stereocenter at C-3 of the pyrrolidine ring. Please consult the Aladdin Scientific product page, Certificate of Analysis, or contact the sales team to confirm whether the compound is supplied as a racemate or as a specific enantiomer (R or S configuration).
What safety precautions should be taken when handling this compound?
As a sulfonyloxy ester and Boc-protected amine, the compound should be handled with standard laboratory precautions: use appropriate personal protective equipment (gloves, lab coat, safety goggles), work in a well-ventilated fume hood, and avoid inhalation of dust or vapors. Consult the Safety Data Sheet (SDS) available on the Aladdin Scientific product page for compound-specific hazard classifications, GHS pictograms, and first-aid measures before use.
How can I obtain a Certificate of Analysis (CoA) or purity specification for T729717?
The Certificate of Analysis and purity data for T729717 can be downloaded directly from the Aladdin Scientific product page by entering the batch or lot number. Alternatively, you may contact Aladdin Scientific customer service with your order details to request documentation. The CoA will confirm purity grade, analytical method (e.g., HPLC or NMR), and any additional quality parameters.
References
- Aladdin Scientific product page for tert-Butyl 3-((tosyloxy)methyl)pyrrolidine-1-carboxylate, SKU T729717.
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: New York, 2007. (General reference for Boc protecting group chemistry.)
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; Wiley: New York, 2001. (General reference for nucleophilic substitution at sulfonate esters.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）