tert-butyl (3R)-3-[(2S)-3-[3-(2-aminoethoxy)phenyl]-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]pyrrolidine-1-carboxylate
[CAS# 2924842-16-8]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives
• Name: tert-butyl (3R)-3-[(2S)-3-[3-(2-aminoethoxy)phenyl]-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]pyrrolidine-1-carboxylate
• Molecular Formula: C₂₄H₃₈N₂O₅
• Molecular Weight: 434.57
• CAS Registry Number: 2924842-16-8
• SMILES: CC(C)(C)OC(=O)[C@@H](CC1=CC(=CC=C1)OCCN)[C@H]2CCN(C2)C(=O)OC(C)(C)C

Discovory and Applicatios

Tert-butyl (3R)-3-[(2S)-3-[3-(2-aminoethoxy)phenyl]-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]pyrrolidine-1-carboxylate is a chiral, heavily protected intermediate used in medicinal chemistry for the synthesis of complex small-molecule therapeutics. The molecule contains a pyrrolidine ring with defined (3R)-stereochemistry, substituted at the 3-position with a side chain bearing a (2S)-configured amino acid derivative. This side chain is functionalized with a 3-(2-aminoethoxy)phenyl group and a tert-butyl-protected hydroxyl group, while the pyrrolidine nitrogen is protected as a tert-butyl carbamate (Boc). The combination of stereochemistry, protecting groups, and functional handles allows for selective transformations in multi-step synthetic sequences.

The aminoethoxyphenyl group provides a nucleophilic site for further derivatization or coupling, while the Boc and tert-butyl ether protecting groups prevent undesired side reactions during synthetic elaboration. The stereogenic centers ensure proper three-dimensional orientation, which is critical for downstream biological activity when incorporated into pharmacologically active scaffolds. This intermediate is typically used in peptide-like or peptidomimetic synthesis, allowing for late-stage modification of the phenyl side chain or installation of additional functional groups.

Handling requires standard precautions for chiral, protected intermediates. It is generally supplied as a high-purity solid, and care should be taken to avoid conditions that would remove protecting groups prematurely or induce racemization. Analytical techniques such as chiral HPLC, NMR spectroscopy, and mass spectrometry are employed to verify stereochemistry, purity, and structural integrity prior to use in further synthetic steps.