(S)-3-(Boc-Amino)pyrrolidine CAS-no-122536-76-9_News

Basic Chemical Information:
(S)-3-(Boc-amino)pyrrolidine, with the unique CAS registration number 122536-76-9, is a crucial chiral nitrogen-containing heterocyclic organic compound widely applied in pharmaceutical synthesis and fine chemical industry. 
Its systematic IUPAC name is tert-butyl N-[(3S)-pyrrolidin-3-yl]carbamate, and it has multiple common synonyms including 3(S)-(tert-butoxycarbonylamino)pyrrolidine and (S)-tert-Butyl pyrrolidin-3-ylcarbamate.
The molecular formula of this compound is C₉H₁₈N₂O₂, with an accurate molecular weight of 186.26 g/mol. It possesses a typical single chiral center at the 3-position of the pyrrolidine ring, presenting stable S-configurational stereoisomerism, 
which is the core structural basis for its stereoselective synthesis applications.

Physical and Chemical Properties:
-- Physical Properties
(S)-3-(Boc-amino)pyrrolidine appears as a colorless to pale yellow transparent liquid or low-melting solid at room temperature and atmospheric pressure.
 It has good solubility in common organic solvents such as methanol, ethanol, dichloromethane, ethyl acetate and tetrahydrofuran, while it is slightly soluble in water and insoluble in non-polar solvents like n-hexane and petroleum ether. 
The compound has stable physical morphology under normal temperature and pressure conditions.
-- Chemical Properties
This chemical contains two key functional groups: a Boc (tert-butyloxycarbonyl) protecting group and a pyrrolidine secondary amine structure. 
The Boc group is a classic amino protective group with excellent chemical stability under alkaline, neutral and mild acidic conditions, which can effectively shield the activity of amino groups and avoid unnecessary side reactions during multi-step synthesis.
In specific acidic environments (such as trifluoroacetic acid and dilute hydrochloric acid), the Boc group can be efficiently and selectively removed to expose free primary amino groups, realizing directional functional group activation.  

Synthetic Routes:
At present, the mainstream industrial and laboratory synthesis of (S)-3-(Boc-amino)pyrrolidine is based on chiral raw material derivation and stereoselective amination reaction, with mature and controllable synthesis processes. 
The most widely used route takes chiral (S)-3-aminopyrrolidine as the starting material. Under low-temperature alkaline conditions (using sodium carbonate or triethylamine as acid-binding agent), it reacts with di-tert-butyl dicarbonate (Boc₂O) in an anhydrous organic solvent.
This reaction can selectively protect the 3-position amino group of the pyrrolidine ring, while retaining the activity of the pyrrolidine ring nitrogen atom. 
After the reaction is completed, the crude product is purified by washing, solvent evaporation and column chromatography or distillation to obtain high-purity target products. 
The whole synthesis process has mild reaction conditions, high stereoselectivity, basically no racemization of chiral centers, high product yield and simple post-treatment, which is suitable for both laboratory small-scale preparation and industrial mass production.

Core Applications:
--Pharmaceutical Intermediate Synthesis
As a high-value chiral building block, (S)-3-(Boc-Amino)pyrrolidine is widely used in the synthesis of small-molecule targeted drugs, central nervous system drugs and antibacterial drugs. 
A large number of studies have shown that it is an important intermediate for the synthesis of bacterial cell division inhibitors, and the derived sulfonamidopyrrolidine compounds have excellent antibacterial activity.
In addition, it is commonly applied in the research and development of anti-inflammatory drugs, analgesic drugs and kinase inhibitor drugs. The Boc protection strategy in the molecule can effectively improve the synthesis efficiency of complex drug molecules and reduce side reactions .
-- Fine Chemical and Biochemical Research
In the field of fine chemicals, this compound serves as a key chiral ligand and synthetic fragment for the preparation of high-value chiral additives and pesticide intermediates. In biochemical research, it is widely used in protein engineering and bioactive molecule modification. 
The controllable deprotection characteristic of its Boc group enables selective modification of amino groups in biomolecules, providing reliable technical support for the study of biomolecular structure and function.
(S)-3-(Boc-amino)pyrrolidine (CAS 122536-76-9) is a mature and high-utilization chiral heterocyclic intermediate. Relying on its stable S-chiral configuration, controllable Boc protection-deprotection characteristics and excellent reaction activity, 
it occupies an important position in pharmaceutical synthesis, biochemical research and fine chemical production.
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