Description

tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate (CAS No. 69610-41-9) is a high-purity chiral building block extensively used in organic synthesis and pharmaceutical research. This compound, with the molecular formula C₁₀H₁₇NO₃, features a Boc-protected (tert-butoxycarbonyl) (2S)-pyrrolidine aldehyde, making it a versatile intermediate for asymmetric synthesis and peptidomimetic applications. Its well-defined stereochemistry (S-configuration) ensures precise control in the construction of complex molecules. Supplied as a clear to pale yellow liquid or low-melting solid, it is rigorously tested for purity (typically ≥95% by HPLC or GC) and stored under optimal conditions to guarantee stability. Ideal for researchers in medicinal chemistry, catalysis, and fine chemical production.

Properties

• CAS Number: 69610-41-9
• Complexity: 232
• IUPAC Name: tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate
• InChI: InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H3/t8-/m0/s1
• InChI Key: YDBPZCVWPFMBDH-QMMMGPOBSA-N
• Exact Mass: 199.12084340
• Molecular Formula: C10H17NO3
• Molecular Weight: 199.25
• SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C=O
• Topological: 46.6
• Monoisotopic Mass: 199.12084340
• Synonyms: tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate, 1,1-dimethylethyl (2s)-2-formyl-1-pyrrolidinecarboxylate, 627-548-9, 69610-41-9, N-BOC-L-Prolinal, Boc-L-prolinal, (S)-1-Boc-2-Formylpyrrolidine, (S)-tert-butyl 2-formylpyrrolidine-1-carboxylate, N-(tert-Butoxycarbonyl)-L-prolinal, Boc-prolinal, MFCD00274186, (S)-N-Boc-pyrrolidine-2-carboxaldehyde, (S)-N-tert-Butoxycarbonyl-2-formylpyrrolidine, N-boc-prolinal, 1-Pyrrolidinecarboxylic acid, 2-formyl-, 1,1-dimethylethyl ester, (2S)-, (S)-Boc-prolinal, n-boc-(s)-prolinal, (S)-N-BOC-prolinal, Boc-L-prolinal, 97%, t-butoxycarbonyl-L-prolinal, SCHEMBL40804, tert-butyl (S)-2-formylpyrrolidine-1-carboxylate, tert-butyl(2S)-2-formylpyrrolidine-1-carboxylate, tert-Butoxycarbonyl-L-prolinal, SCHEMBL2355780, N-tert-butoxycarbonyl-L-prolinal, DTXSID20370439, (S)-N-Boc-2-Formyl-pyrrolidine, N-t-butoxylcarbonyl-(L)-prolinal, YDBPZCVWPFMBDH-QMMMGPOBSA-N, N-t-butyloxycarbonyl-(S)-prolinal, MFCD00801206, (S)-Boc-pyrrolidine-2-carboxaldehyde, AKOS005146339, AKOS015841252, CS-W009096, FB50564, AC-28280, AS-18511, HY-78927, Boc-L-Pro-PAM resin (100-200 mesh), DB-030141, ST50825438, EN300-66989, (S)-t-butyl-2-formylpyrrolidine-1-carboxylate, tert-butyl (2S)-2-formylpyrrolidinecarboxylate, (2S)-N-(tert-butoxycarbonyl)-2-formylpyrrolidine, (5)-tert-butyl 2-formylpyrrolidine-1-carboxylate, tert-butyl (2S)-2-formyl-1-pyrrolidinecarboxylate, tert-butyl (25)-2-formylpyrrolidine-1-carboxylate, (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carbaldehyde, Q63396124, (2S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carbaldehyde, (S)-(-)-1-tert-butoxycarbonyl-2-pyrrolidinecarbaldehyde, Z1065768486, (S)-2-formylpyrrolidine-1-carboxylic acid tert-butyl ester, (2S)-1-(tert-butyloxycarbonyl)-pyrrolidine-2-carboxaldehyde, (S)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester, (S)-2-Formyl-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester, (S)-2-Formyl-1-pyrrolidinecarboxylic Acid, 1.1-dimethylethyl Ester

Application

tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate is widely employed as a key chiral synthon in the asymmetric synthesis of bioactive compounds, including protease inhibitors and peptidomimetics. Its aldehyde functionality enables reductive amination or nucleophilic addition reactions, facilitating the introduction of pyrrolidine scaffolds into drug candidates. The Boc-protecting group enhances solubility and allows selective deprotection under mild acidic conditions. Researchers also utilize it in organocatalysis and ligand design for transition metal complexes.

Safety and Hazards

GHS Hazard Statements

• H226 (85.1%): Flammable liquid and vapor [Warning Flammable liquids]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (91.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (85.1%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (91.5%)

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