168049-26-1

Basic information

• Product Name: (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine
• Synonyms: (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine;(S)-2-(Azidomethyl)-1-(tert-butoxycarbonyl)pyrrolidine;tert-Butyl (S)-2-(azidomethyl)-1-pyrrolidinecarboxylate;(2S)-1-Boc-2-(azidomethyl)-pyrrolidine;(S)-tert-Butyl 2-(azidomethyl)pyrrolidine-1-carboxylate
• CAS NO: 168049-26-1
• Molecular Formula: C₁₀H₁₈N₄O₂
• Molecular Weight: 226.27552
• Mol File: 168049-26-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine(168049-26-1)
• EPA Substance Registry System: (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine(168049-26-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 168049-26-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is used as a building block for the synthesis of complex organic molecules, leveraging its structural components to create a diverse range of compounds.
Used in Click Chemistry:
The azidomethyl group in (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine allows it to be used as a versatile reactant in click chemistry, a set of reactions that are known for their reliability, efficiency, and selectivity, particularly for the formation of triazoles.
Used in Pharmaceutical Industry:
(S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is used as an intermediate in the development of pharmaceutical compounds, where its ability to undergo selective reactions and form complex structures is highly beneficial for creating potential drug candidates.
Used in Materials Science:
In the field of materials science, (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is utilized for the synthesis of novel materials with specific properties, such as polymers and dendrimers, which can have applications in various industries including electronics, medicine, and nanotechnology.
Used in Research and Development:
(S)-2-(AzidoMethyl)-1-Boc-pyrrolidine serves as a key compound in research and development settings, where its unique properties and reactivity are explored for new applications and to advance the understanding of chemical reactions and mechanisms.

Upstream product

• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 1004993-43-4 tert-butyl (2S)-2-[(phenylselenonyl)methyl]pyrrolidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 338945-22-5 (S)-2-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 147-85-3 L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 119020-01-8 (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 174698-95-4 (2S)-2-azidomethyl-pyrrolidine 
• 918134-14-2 C₁₆H₂₃N₃O₆S 
• 168050-40-6 (S)-2-Amino-1-((S)-2-azidomethyl-pyrrolidin-1-yl)-3-benzyloxy-propan-1-one 
• 168050-38-2 [(S)-2-((S)-2-Azidomethyl-pyrrolidin-1-yl)-1-benzyloxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 168050-45-1 Naphthalene-2-sulfonic acid [(S)-2-((S)-2-azidomethyl-pyrrolidin-1-yl)-1-benzyloxymethyl-2-oxo-ethyl]-amide 
• 168050-46-2 Naphthalene-2-sulfonic acid [(S)-2-((S)-2-aminomethyl-pyrrolidin-1-yl)-1-benzyloxymethyl-2-oxo-ethyl]-amide 

Relevant articles and documents

Application of Proline-Derived (Thio)squaramide Organocatalysts in Asymmetric Diels-Alder and Conjugate Addition Reactions

The synthesis of chiral proline-derived squaramide and thiosquaramide organocatalysts, which are capable of the dual activation in asymmetric reactions is reported. The (thio)squaramide moiety can form hydrogen bonds to activate the substrates and to stereocontrol the reaction, while the pyrrolidine unit can form enamines to activate carbonyl compounds via aminocatalysis. Comparing the performance of thiosquaramide to squaramide, the Diels Alder reaction of (anthracen-9-yl)acetaldehyde and trans-?-nitrostyrene was examined, which has been investigated in the literature using quantum chemical calculations. Both squaramide and thiosquaramide gave excellent yields (up to 99%) and enantiomeric excess values (up to 98%). Moreover, their catalytic performance was compared in conjugate addition of lawsone to ?,?-unsaturated ?-keto ester.

Synthesis of Chiral Triazole-Based Halogen Bond Donors

The number of applications that use halogen bonding in the fields of self-assembly, supramolecular aggregation, and catalysis is growing. However, the accessibility of chiral halotriazoles shows that there is still a lot more to explore. The simple click-chemistry is applied for the straightforward synthesis of enantiomerically pure mono- and bidentate as well as multifunctional iodotriazole-based XB donors. The methodology is characterized by a wide variability due to easy access of chiral azides.

Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.

COMPOUNDS FOR REACTIVATION OF ACETYLCHOLINESTERASE AND RELATED COMPOSITIONS METHODS AND SYSTEMS

Described herein are oxime compounds capable of inactivating a nerve agent, blood brain barrier (BBB)-penetration, and/or reactivation of nerve agent-inhibited acetylcholinesterase (AChE) and related methods, systems and compositions for inactivation of one or more nerve agents, therapeutic and/or prophylactic treatment of an individual, and/or decomposition of nerve agent for decontamination.

Pyrrolidine modified PANF catalyst for asymmetric Michael addition of ketones to nitrostyrenes in aqueous phase

Three chiral pyrrolidine functionalized polyacrylonitrile fiber catalysts have been designed, prepared, and evaluated for their catalytic performance in asymmetric Michael addition of ketones to nitrostyrenes in water. With the optimized catalysts and conditions in hand, their reaction scope for nitrostyrenes was explored. Then the fiber catalysts were further applied to a packed-bed reactor for continuous-flow Michael addition. Based on the fact that organic solvent can inhibit the catalytic activity, a novel microenvironment catalytic mechanism is proposed.

Synthesis and in vivo evaluation of 11C-labeled (1,7-dicarba-closo-dodecaboran-1-yl)-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl} amide

Boron clusters, and especially dicarba-closo-dodecaboranes, can be used as hydrophobic pharmacophores in the design of new drugs and radiotracers because of their hydrophobic character, spherical structure, and excellent chemical and photochemical stability. In the present paper, the synthesis and in vivo evaluation of 11C-labeled (1,7-dicarba-closo-dodecaboran-1-yl)-N- {[(2S)-1-ethylpyrrolidin-2-yl]methyl}amide, an analog of the D2 receptor ligand [11C]raclopride, is described. The radiosynthesis was approached by reaction of the demethylated precursor with [11C] CH3I in basic media; moderate radiochemical yields (18.2 ± 2.8%, decay corrected), and excellent radiochemical purities (>98%) were obtained in overall synthesis time of ~50 min. In vivo assays showed a biodistribution pattern with significant uptake in liver, kidneys and lungs at short times (t = 4 min) after administration and increasing accumulation in bladder at longer times (t ≥ 14.5 min). Although brain positron emission tomography scans showed good blood brain barrier penetration, the high unspecific uptake observed in different brain regions impedes its applicability as D2 receptor ligand.

Design, synthesis and catalytic property of L-proline derivatives as organocatalysts for direct aldol reaction

A series of chiral prolinamide compounds with pyridine-2, 6-dicarboxylic acid moieties derived from L-proline have been designed and synthesized, their catalytic properties for direct asymmetric aldol reactions were also studied in this article. These catalysts gave the aldol product in high yield (87%) and high enantioselectivity, up to 85%, of the anti-structure at room temperature but gave disappointing results at a lower temperature or when additive was added. Conditions, including solvents, temperature and additives were screened for the reactions. Moreover, the influence of presence of water on yield and stereoselectivity was also discussed. Copyright

Synthesis of new enantiopure thioureas derived from (S)-proline

Enantiopure thiourea derivatives, containing pyrrolidine ring, were prepared by the reaction of N-Boc-(S)-2-aminomethylpyrrolidine (6) with thioisocyanates 8.

Stereoselective synthesis of chiral pyrrolidine derivatives of (+)-α-pinene containing a β-amino acid moiety

We report the synthesis of several enantiopure pyrrolidine derivatives containing a β-amino acid moiety. These novel chiral compounds were prepared through stereospecific chlorosulfonyl isocyanate (CSI) addition to the readily available, natural terpene (+)-α-pinene. Coupling of N-Boc-protected β-amino acid derivatives with various bulky amines and amino acids using the mixed anhydride activation method, followed by N-deprotection, afforded the corresponding chiral amino amides in good yields. Despite the severe steric hindrance anticipated in α-pinene-based heterocycles, efficient coupling of the amino amides and an amino ester with the acyl chloride of N-Cbz-protected (S)-proline provided the corresponding pyrrolidinic pinene derivatives in good yields. Moreover, a convenient synthesis of N-Cbz- and N-Boc-monoprotected (S)-prolinamine is reported. Georg Thieme Verlag Stuttgart New York.

1-alkyl-5-((di)alkylamino) tetrazoles: Building blocks for peptide surrogates

An approach to the synthesis of 1-alkyl-5-((di)alkylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyltetrazoles with anions generated from the primary or secondary amines was developed. Tolerance of the method to the presence of some fun