Description

tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate (CAS 191347-94-1) is a high-purity chiral building block widely used in pharmaceutical research and organic synthesis. This compound, with the molecular formula C₁₀H₁₇NO₃, features a stereocenter at the 3-position of the pyrrolidine ring, making it a valuable intermediate for asymmetric synthesis. The tert-butyloxycarbonyl (Boc) protecting group enhances stability and facilitates selective deprotection under mild acidic conditions. Its formyl group (–CHO) offers versatile reactivity for nucleophilic additions, reductive aminations, and other key transformations. Supplied as a clear to pale-yellow liquid or low-melting solid, this reagent is rigorously tested for purity (typically ≥95% by HPLC or GC) and stored under inert conditions to ensure optimal shelf life. Ideal for medicinal chemistry, peptidomimetics, and catalyst design.

Properties

• CAS Number: 191347-94-1
• Complexity: 232
• IUPAC Name: tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate
• InChI: InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-5-4-8(6-11)7-12/h7-8H,4-6H2,1-3H3/t8-/m1/s1
• InChI Key: DWLADVOODHZCFV-MRVPVSSYSA-N
• Exact Mass: 199.12084340
• Molecular Formula: C10H17NO3
• Molecular Weight: 199.25
• SMILES: CC(C)(C)OC(=O)N1CC[C@H](C1)C=O
• Topological: 46.6
• Monoisotopic Mass: 199.12084340
• Synonyms: 191347-94-1, tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate, 635-408-3, (R)-tert-butyl 3-formylpyrrolidine-1-carboxylate, (R)-1-Boc-3-pyrrolidinecarbaldehyde, 1-Pyrrolidinecarboxylic acid, 3-formyl-, 1,1-dimethylethyl ester, (3R)-, (3R)-3-FORMYL-1-PYRROLIDINECARBOXYLIC ACID TERT-BUTYL ESTER, (R)-tert-butyl3-formylpyrrolidine-1-carboxylate, SCHEMBL935410, DTXSID00974792, (3R)-1-Boc-3-formylpyrrolidine, (R)-3-formyl-1-Boc-pyrrolidine, DWLADVOODHZCFV-MRVPVSSYSA-N, 1-Pyrrolidinecarboxylic acid, 3-formyl-, 1,1-dimethylethyl ester, (R)-, AKOS024262357, AS-42180, FB153080, CS-0048573, EN300-1697197, tert-butyl (R)-3-formylpyrrolidine-1-carboxylate, (R)-3-Formylpyrrolidine-1-carboxylic Acid t-Butyl Ester

Application

tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate serves as a critical intermediate in the synthesis of chiral pharmaceuticals, particularly for protease inhibitors and neurologically active compounds. Its formyl group enables efficient conjugation with amines or hydrazines to construct complex heterocycles. Researchers utilize this Boc-protected aldehyde in stereoselective reactions to introduce pyrrolidine scaffolds into drug candidates. The compound is also employed in ligand design for asymmetric catalysis.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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