What Is cis-Boc-Aminocyclopropane Methyl Ester and Why Is It Used?

cis-Cyclopropanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester (Aladdin SKU C174931) is a bifunctionally protected cyclopropane derivative bearing a Boc-amino group and a methyl ester on adjacent carbons in the cis (syn) configuration. The strained, rigid cyclopropane ring enforces a defined spatial relationship between the two functional groups, making this compound a valuable conformationally constrained building block.

In medicinal chemistry and peptidomimetic research, constrained analogues are introduced to improve metabolic stability, binding selectivity, and bioavailability of peptide leads. The Boc group provides orthogonal amine protection compatible with standard Fmoc or Cbz solid-phase and solution-phase strategies, while the methyl ester offers a readily hydrolysable or reducible handle for further elaboration.

Chemical Identity, Structure, and Stereochemistry

The compound belongs to the class of cyclopropane amino acid derivatives. The cyclopropane ring carries two substituents in a cis relationship: a methoxycarbonyl (methyl ester) group and a tert-butoxycarbonylamino (NHBoc) group. This cis relative configuration distinguishes it from the corresponding trans isomer, which would place the two groups on opposite faces of the ring.

Key structural features include:

• Ring strain: The cyclopropane ring provides conformational rigidity and a unique electronic environment that can mimic a peptide bond geometry or a gamma-amino acid scaffold.
• Orthogonal protection: The Boc group is removable under mild acid conditions (e.g., TFA in DCM or HCl in dioxane) without affecting the methyl ester; conversely, the ester can be saponified under basic conditions without disturbing the Boc group under controlled temperatures.
• Stereodefined starting material: The defined cis stereochemistry allows stereocontrolled synthesis of target molecules where absolute or relative configuration is critical.

Handling, Storage, and Safety Considerations

As with most Boc-protected amino building blocks, cis-cyclopropanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester should be handled following standard laboratory safety protocols. Specific safety data should be consulted in the product Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

General handling guidelines include:

• Store in a cool, dry, well-ventilated area, away from heat, moisture, and incompatible materials such as strong oxidisers and strong bases.
• Use appropriate personal protective equipment (PPE): lab coat, chemical-resistant gloves, and safety glasses.
• Weigh and handle in a fume hood to minimise inhalation exposure to fine particulates or vapours.
• Reseal packaging promptly under inert atmosphere (nitrogen or argon) if the compound is moisture- or air-sensitive, as determined by the SDS.

Note: Always refer to the official Aladdin Scientific SDS for authoritative hazard classification, first-aid measures, and disposal guidance specific to lot C174931.

Typical Synthetic Applications and Reactivity

The dual-protected cis isomer (C174931) is particularly suited to sequential deprotection and coupling strategies:

• Boc removal followed by amide bond formation: Treatment with TFA liberates the free amine, which can then be coupled to carboxylic acid partners using standard reagents (HATU, EDC/HOBt, etc.) to build peptidomimetic sequences.
• Ester hydrolysis to reveal carboxylic acid: Saponification with LiOH or NaOH provides the free cis-amino acid (still Boc-protected), which can be used directly in peptide coupling reactions.
• Reduction of methyl ester: DIBAL-H or LiAlH4 reduction of the ester gives the corresponding amino alcohol, a useful precursor to cyclopropane-containing heterocycles or further functionalised scaffolds.
• Ring-opening chemistry: Under certain nucleophilic or electrophilic conditions, the activated cyclopropane ring may undergo ring-opening to generate homoallylic or other open-chain intermediates, though controlled conditions are required to avoid undesired side reactions.

The rigid cis geometry enforces close proximity of the amino and ester groups, facilitating intramolecular reactions such as lactamisation under appropriate conditions to yield beta-lactam or diketopiperazine-type products.

Ordering, Availability, and Quality at Aladdin Scientific

cis-Cyclopropanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester is available from Aladdin Scientific under SKU C174931. Researchers and procurement teams can place orders through the Aladdin Scientific website or contact the sales team for bulk pricing, custom pack sizes, and lead-time enquiries.

Quality assurance at Aladdin Scientific typically encompasses identity confirmation by NMR and/or MS, purity assessment by HPLC or GC, and lot-specific Certificates of Analysis (CoA) available on request. Customers are encouraged to review the CoA for the specific lot received to confirm compliance with their application requirements.

For questions regarding payment, pricing, promotions, returns, shipping, or account management, please contact Aladdin Scientific customer service directly via the support portal.