122536-76-9

Basic information

• Product Name: (S)-3-(Boc-amino)pyrrolidine
• Synonyms: N-(3S)-(-)-3-(T-BUTOXYCARBONYL)AMINOPYRROLIDINE;(S)-TERT-BUTYL-PYRROLIDINE-3-YLCARBAMATE;(S)-PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER;TERT-BUTYL (S)-3-PYRROLIDINYLCARBAMATE;TERT-BUTYL (S)-PYRROLIDIN-3-YL CARBAMATE;(S)-(-)-3-(BOC-AMINO)PYRROLIDINE;(S)-(+)-3-(BOC-AMINO)PYRROLIDINE;(S)-3-(BOC-AMINO)PYRROLIDINE
• CAS NO: 122536-76-9
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25
• EINECS: -0
• Product Categories: N-BOC;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;pharmacetical;Pyrrole&Pyrrolidine&Pyrroline;API intermediates;Benzenes;3-Aminopyrrolidines;Amines (Chiral);Chiral 3-Aminopyrrolidines;Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 122536-76-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 50 °C
• Boiling Point: 112°C/0.25mm
• Flash Point: 127 °C
• Appearance: White to off-white/Powder
• Density: 1.04 g/cm³
• Vapor Pressure: 0.00264mmHg at 25°C
• Refractive Index: -20 ° (C=1, EtOH)
• Storage Temp.: Room temperature.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.37±0.20(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• BRN: 5377813
• CAS DataBase Reference: (S)-3-(Boc-amino)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(Boc-amino)pyrrolidine(122536-76-9)
• EPA Substance Registry System: (S)-3-(Boc-amino)pyrrolidine(122536-76-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: 3259
• WGK Germany: 3
• F: 10-23
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 122536-76-9(Hazardous Substances Data)

Usage

Description

(S)-3-(Boc-amino)pyrrolidine is a chiral, white crystalline powder that serves as a versatile building block in organic synthesis and pharmaceutical chemistry. Its unique structure and properties make it a valuable component in the development of various biologically active compounds.

Uses

Used in Pharmaceutical Industry:
(S)-3-(Boc-amino)pyrrolidine is used as a key intermediate for the synthesis of 2,4,6-trisubstitued pyrido[3,4-d]pyrimidine derivatives, which are potent inhibitors against EGFR tyrosine kinase. These inhibitors have potential applications in the treatment of various cancers by targeting the epidermal growth factor receptor, a key player in cell proliferation and tumor growth.
Used in Organic Synthesis:
(S)-3-(Boc-amino)pyrrolidine is used as a chiral building block in the asymmetric Morita-Baylis-Hillman reaction. This reaction is a powerful method for the synthesis of chiral functionalized molecules, which are important in the development of pharmaceuticals, agrochemicals, and other bioactive compounds.
Used in Antibacterial Agents:
(S)-3-(Boc-amino)pyrrolidine is used as a precursor for the synthesis of N-benzyl-3-sulfonamidopyrrolidines, which are potent bacterial cell division inhibitors. These compounds have the potential to be developed into new antibiotics to combat drug-resistant bacterial infections.

InChI:InChI=1/C9H18N2O2/c1-9(2,3)13-8(12)11-7-4-5-10-6-7/h7,10H,4-6H2,1-3H3,(H,11,12)/t7-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 79286-79-6 (3S)-3-aminopyrrolidine 
• 185057-49-2 (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinecarboxylic acid,phenylmethyl ester 
• 16596-41-1 N-aminopyrrolidine 
• 131852-53-4 (S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 176970-13-1 [(S)-2-(tert-butoxycarbonyamino)butane-1 ,4-diyl dimethanesulfonate] 
• 176970-11-9 (S)-1-allyl-3-(t-butoxycarbonylamino)pyrrolidine 
• 122536-74-7 (S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-1-pyrrolidinecarboxylic acid phenylmethyl ester 

Downstream Products

• 791838-49-8 {1-[2-(4-phenyl-butyl)-benzofuran-4-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester 
• 1417521-25-5 C₁₆H₁₇FN₆ 
• 1201176-16-0 tert-butyl (R)-[1-(2-chloropyrimidin-4-yl)pyrrolidin-3-yl]carbamate 

Relevant articles and documents

Synthesis and evaluation of novel ligands for the histamine H4 receptor based on a pyrrolo[2,3-d]pyrimidine scaffold

Starting from a known H4R ligand based on a pyrimidine skeleton, a series of novel analogues based on a pyrrolo[2,3-d]pyrimidine scaffold have been prepared. Whereas the original pyrimidine congener shows good affinity at hH4R (Ki = 0.5 μM), its lacks selectivity with a K i value for the hH3R of 1 μM. Within the newly synthesized pyrrolo[2,3-d]pyrimidines, several congeners show Ki values of less than 1 μM at the hH4R and show a much improved selectivity profile. Therefore, these series represent an interesting starting point for the discovery of novel hH4R ligands.

Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry

Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1- methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee.

Methods of treating insulin resistance syndrome and diabetes

This invention is directed to methods of treating insulin resistance syndrome and diabetes in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound derived from adenosine and analogues thereof, or a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof, or a pharmaceutical composition comprising such compound.