(2S,4S)-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate, CAS No. 102195-79-9

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102195-79-9

Catalog No. EBD28002

CAS 102195-79-9

Name (2S,4S)-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

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Basic Information

Synonyms: Boc-cis-Hyp-OMe N-Boc-cis-4-Hydroxy-L-prolinemethylester 1-tert-butyl2-methyl4-hydroxypyrrolidine-1,2-dicarboxylate 1-tert-butyl2-methyl(2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate N-T-Boc-Cis-4-Hydroxyl-L-ProlineMethylEster 1-tert-butyl2-methylcis-4-hydroxypyrrolidine-1,2-dicarboxylate cis-Boc-Hyp-Ome (2S,4S)-1-tert-Butyl2-methyl4-hydroxypyrrolidine-1,2-dicarboxylate

Molecular Formula: C11H19NO5

Molecular Weight: 245.27

MDL Number: MFCD00237541

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

N-Boc-cis-4-hydroxy-L-proline methyl ester is a protected derivative of the non-proteinogenic amino acid cis-4-hydroxy-L-proline. It features a Boc-protected secondary amine and a methyl ester group on the carboxylic acid, making it a versatile chiral building block. The cis configuration of the hydroxyl group on the proline ring is a key structural feature. This compound is primarily used as a crucial intermediate in the synthesis of complex pharmaceutical agents. Its chiral, functionalized pyrrolidine scaffold is a valuable motif found in numerous bioactive molecules, including protease inhibitors, antiviral drugs, and other therapeutic candidates. The orthogonal protecting groups (Boc and methyl ester) allow for selective deprotection and further functionalization, facilitating its incorporation into peptide mimetics and other drug-like structures. As a specialty chiral synthon, it is a staple in medicinal chemistry research for constructing constrained peptide analogs and exploring structure-activity relationships. It is commercially available from fine chemical suppliers catering to pharmaceutical R&D and process chemistry.

Physical Properties

Melting Point: 82-86 °C(lit.)

Boiling Point: 335.244 °C at 760 mmHg

Flash Point: 156.55 °C

Density: 1.216 g/cm3

Storage: -15°C