benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate

• CAT Number: L013433
• CAS Number: 1428243-26-8
• Molecular Formula: C16H20BrNO3
• Molecular Weight: 354.24
• Purity: ≥95%
• IUPAC Name: benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
• InChI: InChI=1S/C16H20BrNO3/c1-2-13-9-18(10-14(13)15(19)8-17)16(20)21-11-12-6-4-3-5-7-12/h3-7,13-14H,2,8-11H2,1H3/t13-,14+/m1/s1
• InChIKey: QEFUCTKHMXMWRF-KGLIPLIRSA-N
• SMILES: CC[C@@H]1CN(C[C@@H]1C(=O)CBr)C(=O)OCC2=CC=CC=C2

Benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate(CAT: L013433) is a stereochemically defined pyrrolidine derivative featuring a benzyl carbamate-protected nitrogen, a bromoacetyl substituent at the 3-position, and an ethyl group at the 4-position. The (3R,4S) configuration provides chirality crucial for applications in asymmetric synthesis and drug design. The electrophilic bromoacetyl moiety is highly reactive, enabling alkylation, acylation, and nucleophilic substitution reactions—useful for generating covalent inhibitors or peptidomimetic intermediates. This compound is often employed in medicinal chemistry for constructing structurally complex molecules, particularly those targeting serine hydrolases or cysteine-based enzymes, due to its potential to form stable, functionalized heterocycles and enzyme-bound intermediates.