Product Overview

This product is a Boc protected, stereodefined pyrrolidine amino acid ester supplied as the hydrochloride salt. It carries a tert-butoxycarbonyl protected secondary amine at the ring nitrogen, a free primary amine at the 4 position, and a methyl ester at the 2 position, with the (2R,4S) configuration. The material is a white to yellow solid and is used as a chiral building block in peptide and peptidomimetic synthesis and in the preparation of nitrogen heterocycle containing pharmaceutical intermediates.

Key Attributes

Key Highlights

• DEFINED STEREOCHEMISTRY: Supplied as the single (2R,4S) stereoisomer, so the configuration is carried through the synthesis without the need for a later resolution or chiral separation step.
• ORTHOGONAL PROTECTION: The Boc group on the ring nitrogen and the methyl ester at the 2 position can be removed independently, while the 4 position primary amine stays free for direct coupling, alkylation, acylation or sulfonylation.
• CONSTRAINED PYRROLIDINE SCAFFOLD: The five membered ring limits rotatable bonds and fixes the spatial relationship between the two functionalized positions, which is valuable when a defined three dimensional presentation is required.
• HIGH PURITY: Assay not less than 95.0%, with a certificate of analysis issued for every lot to support your incoming verification.
• STABLE SALT FORM: Delivered as the hydrochloride salt, which improves handling and weighing behaviour compared with the free base and simplifies dissolution in polar reaction media.
• FULLY DOCUMENTED IDENTITY: Registered under EC No. 897-808-6 and MDL No. MFCD10568359, with a unique InChI Key, so the exact stereoisomer you order can be traced unambiguously in your records.
• FLEXIBLE PACK SIZE: Minimum order quantity is 1 g, with unit packs available from 1 g up to 1 kg so that route screening and scale up work can use the same material.
• FAST LEAD TIME: Orders are normally dispatched within 7 working days after confirmation, shipped by courier or by air in sealed, light protected packaging.

Product Description

(2R,4S)-4-Amino-1-Boc-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (CAS 1217446-43-9) is a chiral pyrrolidine building block with the molecular formula C11H21ClN2O4 and a molecular weight of 280.75 g/mol. The molecule is built on a pyrrolidine ring carrying three differentiated functional groups: a tert-butoxycarbonyl protected secondary amine on the ring nitrogen, a free primary amine at the 4 position, and a methyl ester at the 2 position. The two ring carbons at positions 2 and 4 are stereogenic centres, and this product is supplied as the defined (2R,4S) stereoisomer rather than as a diastereomeric or racemic mixture. The material is a white to yellow solid and is offered with an assay of not less than 95.0%.

The practical value of this compound lies in its orthogonally protected, multifunctional design. The 4 position amine is already deprotected and ready to react, so it can be coupled to a carboxylic acid, acylated, sulfonylated, alkylated or converted into an amide, urea or sulfonamide without a prior deprotection step. The Boc group can later be cleaved under acidic conditions to release the ring nitrogen for a second coupling or cyclization, and the methyl ester can be hydrolysed to the free acid or converted to an amide or alcohol. Because the ring is conformationally constrained, the relative orientation of these two positions is fixed, which is often the reason a pyrrolidine scaffold is selected over an acyclic amino acid in the design of enzyme inhibitors and ligands for protein binding sites. Being supplied as the hydrochloride salt also makes the product easier to weigh, less prone to oiling out, and more straightforward to dissolve in polar media than the corresponding free base.

We supply this product in unit packs from 1 g to 1 kg, with a minimum order quantity of 1 g and a normal lead time within 7 working days. The product is stored at room temperature in a dark place under an inert atmosphere, so shipments move by courier or by air in sealed, light protected and moisture protected packaging. Each lot is released with a certificate of analysis stating the assay, the appearance and the stereochemical identity. Additional technical documents can be provided on request to support your structure confirmation work.

Potential Applications

Peptide and Peptidomimetic Synthesis
Boc protected pyrrolidine amino acid esters of this type may be used as constrained residues in peptide and peptidomimetic chains. The ring restricts backbone flexibility, and the free 4 position amine may be used as an additional attachment point for side chain elaboration or for cross linking within a sequence.

Pharmaceutical Intermediate Synthesis
The product is a candidate building block for active pharmaceutical ingredient routes and for advanced intermediates that require a stereodefined, doubly functionalized pyrrolidine unit. The methyl ester may be carried forward as an acid, an amide or a reduced alcohol, which makes the compound suitable as a branching point in multi step synthesis.

Enzyme Inhibitor and Ligand Design
4-Aminopyrrolidine-2-carboxylic acid scaffolds are widely used in medicinal chemistry programmes that target proteases and protein binding domains. This stereoisomer may be used in structure activity relationship studies where a specific ring configuration is required, and in the preparation of inhibitor series that compare the effect of stereochemistry on binding affinity.

PROTAC and Linker Chemistry
Rigidified pyrrolidine units may be used as conformational elements within linker systems, including targeted protein degradation constructs, where controlling the distance and orientation between the two ends of the linker is important for activity.

Compound Library and Diversity Oriented Synthesis
The combination of three independently addressable functional groups on a small chiral scaffold makes the product useful as a diversity building block for combinatorial and library synthesis programmes.

Asymmetric Synthesis and Catalyst Ligand Development
Chiral pyrrolidine derivatives may be used as precursors to organocatalysts and to chiral ligand frameworks, and as stereochemical references in method development work.

Research and Analytical Use
The product may also be used as a reference material for analytical method development, for chromatographic separation studies on stereoisomers, and for enzyme kinetics or receptor ligand interaction work that relies on a defined chiral structure.

Note: The entries above describe the general use profile of Boc protected 4-aminopyrrolidine-2-carboxylate building blocks. The sections on PROTAC and linker chemistry, compound library synthesis, asymmetric catalysis and analytical reference use are based on the structural features of this molecule and on the reported use of closely related pyrrolidine scaffolds, rather than on product specific published applications. Please confirm suitability for your own process before scale up.

Specifications

Packaging and Shipping

Storage Recommendations

• Store at room temperature in a cool and dry place.
• Keep in a dark place, protected from light at all times.
• Keep under an inert atmosphere of argon or nitrogen.
• Keep the container tightly closed to avoid moisture uptake.
• Store in the original container and keep away from heat.

Minimum order quantity is 1 g. Normal lead time is within 7 working days after order confirmation. Goods are shipped by courier or by air in sealed, light protected and moisture protected packaging with cushioning material. Every shipment includes the certificate of analysis and the packing list.

Company Profile

Dideu Group is a professional supplier of fine chemicals and specialty chemicals, serving customers in global markets with a full range of products from lab scale reagents to industrial quantities. Our portfolio covers chiral building blocks, protected amino acid derivatives, heterocyclic intermediates and custom research chemicals used in pharmaceutical development, agrochemical research and academic synthesis. We work with qualified production partners and apply strict incoming and outgoing quality control, with a certificate of analysis issued for every lot we ship. Our sales and technical team supports customers through product selection, documentation preparation and logistics coordination from inquiry to delivery. Trial packs and larger commercial quantities are handled through the same quality process, so scale up does not require requalification of the material. Send us your target specification, stereochemical requirement and quantity and we will respond with a quotation.

FAQ

What is the minimum order quantity?

Our minimum order quantity is 1 g. Unit packs are available from 1 g up to 1 kg, and larger quantities can be arranged on request, so both route screening and scale up work can be served from the same material.

What is the lead time?

Orders are normally dispatched within 7 working days after order confirmation and receipt of payment.

What packaging options do you offer?

Small quantities are packed in 1 g, 5 g, 10 g and 25 g amber glass bottles with sealed caps and light protection. Larger quantities of 100 g, 500 g and 1 kg are packed in sealed HDPE bottles or aluminium foil bags. All packs are placed in an outer carton with moisture and light protection for transport.

What payment terms do you accept?

We accept T/T and L/C. The specific terms can be confirmed with our sales team according to order value and destination.

Do you provide a COA and technical documents?

Yes. A certificate of analysis is issued for every shipment and states the assay, the appearance and the stereochemical identity of the lot. Additional technical documents can be provided on request to support your structure confirmation work.

How do you ship the goods?

Goods are shipped by courier or by air. The product is stored at room temperature, so shipments are packed in sealed containers with light and moisture protection to keep the material stable during transport.