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

General Description

(S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is a chemical compound that consists of a pyrrolidine ring with a Boc (tert-butoxycarbonyl) protecting group and an azidomethyl group attached to the nitrogen atom. The compound is used as a building block in organic synthesis and can undergo various reactions to form more complex molecules. The azidomethyl group makes it a versatile compound for further derivatization through click chemistry and other reactions. The Boc protecting group also provides a way to selectively modify the compound in organic synthesis. Overall, (S)-2-(AzidoMethyl)-1-Boc-pyrrolidine is a valuable intermediate for the preparation of a wide range of organic compounds.

Upstream product

• 338945-22-5 (S)-2-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 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 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1004993-43-4 tert-butyl (2S)-2-[(phenylselenonyl)methyl]pyrrolidine-1-carboxylate 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 

Downstream Products

• 119020-01-8 (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 863671-47-0 tert-butyl (2S)-2-({5-[(4-methylphenyl)sulfonyl]-1H-tetrazol-1-yl}methyl)pyrrolidine-1-carboxylate 
• 1123889-54-2 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride 
• 1321848-81-0 C₂₀H₁₈F₆N₄OS 
• 174698-95-4 (2S)-2-azidomethyl-pyrrolidine 
• 66411-54-9 1-[(2S)-1-methylpyrrolidin-2-yl]methanamine 

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.