(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
[CAS# 1428243-26-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
• Synonyms: benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
• Molecular Formula: C₁₆H₂₀BrNO₃
• Molecular Weight: 354.24
• CAS Registry Number: 1428243-26-8
• SMILES: CC[C@@H]1CN(C[C@@H]1C(=O)CBr)C(=O)OCC2=CC=CC=C2

Properties

• Solubility: Practically insoluble (0.043 g/L) (25 °C), Calc.^*
• Density: 1.361±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314
• Safety Statements: P280-P305+P351+P338-P310

Discovery and Applications

(3R,4S)-3-(2-bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid benzyl ester is an interesting compound that has attracted much attention in organic and medicinal chemistry. The synthesis of this compound focuses on creating chiral molecules with specific functional groups. Its structure includes a pyrrolidine ring with a 2-bromoacetyl group, an ethyl substituent, and a benzyl ester. This arrangement not only makes the compound structurally unique, but also enhances its reactivity and potential interactions with biological targets.

In medicinal chemistry, the therapeutic potential of (3R,4S)-3-(2-bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid benzyl ester is being explored. The reactivity introduced by the bromoacetyl group can be used in drug development, especially for designing molecules that interact with specific biological pathways. Its unique structure makes it a candidate for investigation of new treatments for various diseases, including those that require precise molecular interactions.

In addition to its medicinal applications, this compound has several other potential uses. It is an important intermediate in organic synthesis and helps in the creation of more complex molecules. Its stereochemistry can be used in asymmetric synthesis to produce enantiomerically pure compounds.

The effects of this compound on neurotransmitter systems have been studied, which could help in the study of neurological diseases.

In materials science, the chemical properties of this compound can be used to develop new materials such as specialized polymers or coatings.

Its reactive groups make it useful for labeling or attaching molecules for imaging or drug delivery.

References

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DOI: 10.1007/s00216-024-05541-0

2022. Synthesis of Upadacitinib. Synfacts, 18, 6.
DOI: 10.1055/s-0041-1738394

2020. Upadacitinib. Pharmaceutical Substances, 1, 1.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-21-0010