119020-01-8

Basic information

• Product Name: (S)-1-N-Boc-2-(aminomethyl)pyrrolidine
• Synonyms: tert-Butyl 2-(1-aminoethyl)-1-pyrrolidinecarboxylate;(S)-TERT-BUTYL-2-(AMINOMETHYL)PYRROLIDINE-1-CARBOXYLATE;RARECHEM AL BW 2320;(S)-2-AMINOMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;(S)-2-(AMINOMETHYL)-1-N-BOC-PYRROLIDINE;(S)-2-AMINOMETHYL-1-BOC-PYRROLIDINE;(S)-1-BOC-2-(AMINOMETHYL)PYRROLIDINE;(S)-1-N-Boc-2-(aminomethyl)pyrrolidine
• CAS NO: 119020-01-8
• Molecular Formula: C₁₀H₂₀N₂O₂
• Molecular Weight: 200.28
• Product Categories: pharmacetical;Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 119020-01-8.mol

Chemical Properties

• Boiling Point: 98-112℃/1mm
• Flash Point: 123.3 °C
• Appearance: /
• Density: 1.044 g/cm³
• Vapor Pressure: 0.0038mmHg at 25°C
• Refractive Index: 1.4670-1.4710
• Storage Temp.: 2-8°C
• Solubility: Miscible with N-methylpyrrolidinone.
• PKA: 9.91±0.29(Predicted)
• BRN: 8905233
• CAS DataBase Reference: (S)-1-N-Boc-2-(aminomethyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-N-Boc-2-(aminomethyl)pyrrolidine(119020-01-8)
• EPA Substance Registry System: (S)-1-N-Boc-2-(aminomethyl)pyrrolidine(119020-01-8)

Safety Data

• Hazard Codes: Xi,N,C
• Statements: 36/37/38-51/53-34-22
• Safety Statements: 26-36/37/39-61-45
• RIDADR: 3259
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 119020-01-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-1-N-Boc-2-(aminomethyl)pyrrolidine is used as an intermediate in organic synthesis for the development of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for the creation of complex molecules with specific stereochemistry, which is crucial for the biological activity and selectivity of the final products.
Used in Synthetic Chemistry:
In synthetic chemistry, (S)-1-N-Boc-2-(aminomethyl)pyrrolidine serves as a chiral and heterocyclic building block. Its incorporation into larger molecules can provide novel properties and functionalities, making it a valuable component in the design and synthesis of advanced materials, catalysts, and other specialty chemicals.
Used in Pharmaceutical Industry:
(S)-1-N-Boc-2-(aminomethyl)pyrrolidine is used as a key component in the synthesis of various pharmaceuticals, particularly those with chiral centers. Its presence in the final drug molecule can significantly influence the drug's efficacy, safety, and pharmacokinetic properties, making it an essential part of the drug development process.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-1-N-Boc-2-(aminomethyl)pyrrolidine is employed in the development of chiral pesticides, herbicides, and other crop protection agents. Its incorporation into these molecules can enhance their selectivity and reduce the environmental impact, leading to more sustainable and effective agricultural practices.
Used in Specialty Chemicals:
(S)-1-N-Boc-2-(aminomethyl)pyrrolidine is also utilized in the production of specialty chemicals, such as chiral ligands, catalysts, and other high-value compounds. Its unique properties and reactivity make it an attractive building block for the development of innovative products with specific applications in various industries, including materials science, electronics, and biotechnology.

InChI:InChI=1/C10H20N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(12)7-11/h8H,4-7,11H2,1-3H3/t8-/m1/s1

Upstream product

• 69610-41-9 Boc-L-Pro-H 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86661-32-7 (S)-tert-butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 168049-26-1 tert-butyl (2S)-2-(azidomethyl)-1-pyrrolidinecarboxylate 
• 147-85-3 L-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 228244-04-0 tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate 
• 281197-55-5 tert-butyl (S)-2-((1,3-dioxoisoindolin-2-yl)methyl)pyrrolidine-1-carboxylate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 1123889-54-2 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea hydrochloride 
• 1321848-81-0 C₂₀H₁₈F₆N₄OS 
• 1443990-10-0 C₁₈H₂₇N₃O₃S 
• 1443990-16-6 C₁₃H₁₉N₃OS 
• 1443990-11-1 C₁₇H₂₄N₄O₄S 
• 1443990-17-7 C₁₂H₁₆N₄O₂S 
• 1443990-12-2 C₁₈H₂₇N₃O₂S 
• 1443990-18-8 C₁₃H₁₉N₃S 
• 1443990-13-3 C₁₉H₂₉N₃O₂S 
• 1123088-49-2 C₁₄H₂₁N₃S 
• 1402805-96-2 (S)-2-(((2-((3,5-bis(trifluoromethyl)benzyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate 
• 1402805-95-1 (S)-2-(((2-((3,5-bis(trifluoromethyl)phenyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate 
• 1394122-54-3 C₂₉H₃₁F₃N₈O₂S₂ 

Relevant articles and documents

Condensation approach to aliphatic oligourea foldamers: Helices with N-(Pyrrolidin-2-ylmethyl)ureido junctions

Caught in a fold: A simple and efficient coupling strategy to make aliphatic oligourea foldamers is reported. Crystal structures show that the pyrrolidine units (red; see picture) do not impair the 2.5-helical folding of the oligoureas. This modular strategy enables assembly of long helical segments containing non-adjacent pyrrolidine units as exemplified by the synthesis of a helix that is approximately 40 long.

N-arenesulfonyl-2-aminomethylpyrrolidmes - Novel modular ligands and organocatalysts for asymmetric catalysis

A novel series of (S)-N-arenesulfonyl-2-aminomethylpyrrolidines were prepared in high overall yield starting from N-Boc-L-proline. The mono-sulfonyldiamines were evaluated as organocatalysts in the asymmetric α-amination of propanal using diethyl azadicarboxylate (DEAD) as the amine source. The initially formed α-aminated aldehyde was reduced in situ to the corresponding N-aminooxazolidinone, which was obtained in moderate to high yield in up to 87% ee.

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.

Synthesis of D2 receptor ligand analogs incorporating one dicarba-closo-dodecaborane unit

Boron clusters, and especially dicarba-closo-dodecaboranes, can be used as hydrophobic pharmacophores in the design of new drugs and radiotracers. In the current Letter, analogs of enantiomeric substituted benzamides (Raclopride and FLB-457) in which the phenyl ring has been substituted by a carborane cage (either orto- or meta-carborane) have been developed as potential D2 receptor antagonists. The formation of intramolecular hydrogen bonds (in solution) and the stability of the new chemical entities have been evaluated by means of 1H NMR and HPLC-MS, respectively.

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.

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

The synthesis of bifunctional N-sulfinylureas and thioureas with an appended pyrrolidine unit is presented. These organocatalysts were evaluated in Michael additions of aldehydes to nitroalkenes both under solvent-free conditions and in solution. The N-su

D -Prolyl-2-(trifluoromethylsulfonamidopropyl)pyrrolidine: An Organocatalyst for Asymmetric Michael Addition of Aldehydes to β-Nitroalkenes at Ambient Conditions

Four 2-(trifluoromethylsulfonamidoalkyl)pyrrolidines and their d-prolinamides were prepared and screened as organocatalysts for the Michael addition reaction of aldehydes with β-nitroalkenes at rt and without the use of additives. d-Prolyl-2-(trifluoromet

BENZIMIDAZOLE-LINKED INDOLE COMPOUND ACTING AS NOVEL DIVALENT IAP ANTAGONIST

The present invention discloses a benzimidazole-linked indole compound acting as novel divalent IAP antagonist, specifically disclosing the compound shown in fomulas (I) or a pharmaceutically acceptable salt thereof.

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.