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
• Article Data: 30

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

Description

(S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is a chemical compound that features a pyrrolidine ring with a Boc (tert-butoxycarbonyl) protecting group and an azidomethyl group attached to the nitrogen atom. (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is recognized for its role as a building block in organic synthesis, allowing for the creation of more complex molecules through various reactions. The presence of the azidomethyl group endows it with versatility for further derivatization via click chemistry and other reactions, while the Boc protecting group enables selective modification in organic synthesis. (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is thus a valuable intermediate for preparing a broad spectrum of organic compounds.

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 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 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 

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.

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.

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.