Description

tert-Butyl (2R,3R)-2-cyano-3-hydroxypyrrolidine-1-carboxylate (CAS No. 2227198-23-2) is a high-purity chiral intermediate designed for pharmaceutical research and fine chemical synthesis. With the molecular formula C₁₀H₁₆N₂O₃, this compound features a stereochemically defined pyrrolidine scaffold with cyano and hydroxyl functional groups, making it an invaluable building block for asymmetric synthesis and drug development. Its tert-butyloxycarbonyl (Boc) protecting group ensures stability during complex reactions, while the (2R,3R) configuration enables precise stereocontrol. Ideal for medicinal chemists and process researchers, this reagent is supplied with rigorous QC validation (≥95% purity by HPLC) and is available in scalable quantities under inert packaging to maintain integrity. Store at 2-8°C in a dry environment.

Properties

• CAS Number: 2227198-23-2
• Complexity: 300
• IUPAC Name: tert-butyl (2R,3R)-2-cyano-3-hydroxy-pyrrolidine-1-carboxylate
• InChI: InChI=1S/C10H16N2O3/c1-10(2,3)15-9(14)12-5-4-8(13)7(12)6-11/h7-8,13H,4-5H2,1-3H3/t7-,8-/m1/s1
• InChI Key: LKHZFNXKDVXDPA-HTQZYQBOSA-N
• Exact Mass: 212.11609238
• Molecular Formula: C10H16N2O3
• Molecular Weight: 212.25
• SMILES: CC(C)(C)OC(=O)N1CC[C@H]([C@H]1C#N)O
• Topological: 73.6
• Monoisotopic Mass: 212.11609238
• Synonyms: 2227198-23-2, tert-Butyl (2R,3R)-2-cyano-3-hydroxypyrrolidine-1-carboxylate, tert-butyl (2R,3R)-2-cyano-3-hydroxy-pyrrolidine-1-carboxylate

This compound serves as a versatile chiral synthon in the synthesis of bioactive molecules, particularly protease inhibitors and peptidomimetics. Its hydroxyl and cyano groups facilitate further derivatization, while the Boc group allows selective deprotection under mild acidic conditions. Researchers utilize it in stereoselective transformations, such as nucleophilic additions or cyclizations, to access complex heterocycles. It is also employed in the development of CNS-targeting therapeutics due to its pyrrolidine core.

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