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

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

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

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

Downstream Products

• 178688-10-3 ((S)-1-Cyclohexyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester 
• 791838-49-8 {1-[2-(4-phenyl-butyl)-benzofuran-4-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester 
• 852324-85-7 (3S)-1-(2-nitrobenzene)sulfonyl-3-BOC-aminopyrrolidine 
• 474774-40-8 (1-m-tolyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester 
• 952406-60-9 tert-butyl (3S)-1-quinolin-5-ylpyrrolidin-3-ylcarbamate 
• 959918-35-5 3-({(3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidin-1-yl}carbonyl)phenylboronic acid 
• 100-46-9 benzylamine 
• 1013920-62-1 C₁₁H₂₀N₂O₃ 
• 299203-95-5 (3-tert-butoxycarbonylamino-pyrrolidin-1-yl)-acetic acid 
• 1055726-90-3 [(S)-1-(2,2-diphenyl-ethyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 
• 1055726-92-5 [(S)-1-(3,3-diphenyl-propionyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 
• 762285-42-7 {(S)-1-[((S)-1-Benzyl-pyrrolidin-3-yl)-methyl-carbamoyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester 

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.

STEREOSELECTIVE SYNTHESIS OF PIPERIDINE DERIVATIVES

This invention relates to dialdehyde or dinitrile compounds, which are useful for stereoselective synthesis of piperidine, pyrrolidine, and azepane derivatives.

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.

PROCESS FOR PRODUCING NITROGENOUS HETEROCYCLIC COMPOUND

A nitrogenous heterocyclic compound such as 3-aminopyrrolidine derivative is produced by hydrogenolysis of an N-substituted nitrogenous heterocyclic compound with normal pressure hydrogen in a water-based solvent in presence of a catalyst. In the case an optically active 1-substituted-3-aminopyrrrolidine derivative is used as a raw material, an optically active 3-aminopyrrolidine derivative can be obtained as a product practically without racemination.

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.

Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties

A compound of the formula wherein K is N; Q is CH2or O; R6is hydrogen, alkyl, allyl, 2-methylallyl, 2-butenyl, or cycloalkyl where the nitrogen of the ring of X is substituted by Y; E is O or S; Y is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, or substituted heterocyclylalkyl; and n and p are independently 0, 1, 2, or 3, provided that n+p is at least 1; T is hydrogen, alkyl, alkylcarbonyl, alkylthiocarbonyl, halo, carboxyl, A and B are independently hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, or OR′; or a pharmaceutically acceptable salt thereof, a pharmaceutic-ally acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof.

An efficient conversion of chiral α-amino acids to enantiomerically pure 3-amino cyclic amines

Enantiomerically pure 3-amino cyclic amines such as 3-amino pyrrolidine, 3-amino piperidine, and 2,3,4,5,6,7-hexahydro-1H-azepine have been synthesized in high yields from the optically active natural α-amino acids such as L-aspartic acid, L-glutamic acid, L-2-aminoadipic acid, and their enantiomers.

Practical synthesis of (S)-3-(p-nitrobenzyloxy-carbonylamino)pyrrolidine and its related compounds from L-aspartic acid

An efficient method for the preparation of (S)-3-aminopyrrolidine derivatives was developed starting from L-aspartic acid, which involves an efficient formation of a pyrrolidine-ring from allylamine and a practical Pd/C-catalyzed cleavage of N-allyl prote

Quinobenzoxazine, antineoplastic agents

Quinobenzoxazine, derivatives of the formula STR1 as well as the pharmaceutically acceptable salts, esters, amides and prodrugs thereof are disclosed, wherein R1 is hydrogen or a carboxy-protecting group, R2 and R3 are substitutents, A is oxygen, Z is a halogen or a nitrogen-containing group, X is hydrogen, halogen or alkyl, and W is hydrogen, alkyl, amino or halogen. The compounds have potent antineoplastic activity.

Quinolone antibacterial agents. Synthesis and structure-activity relationships of a series of amino acid prodrugs of racemic and chiral 7-(3- amino-1-pyrrolidinyl)quinolones. Highly soluble quinolone prodrugs with in vivo pseudomonas activity

A series of amino acid prodrugs of racemic and chiral 7-(3-amino-1- pyrrolidinyl)-6-fluoro-1,8-naphthyridine-3-carboxylic acids, 1-cyclopropyl- 6,8-difluoro-3-quinolinecarboxylic acids, 1-cyclopropyl-6-fluoro-3- quinolinecarboxylic acids, and 5-amino-1-cyclopropyl-6,8-difluoro-3- quinolinecarboxylic acids have been prepared and evaluated for comparative antibacterial activity. Compounds were prepared by acylation of the 3-amino group of the pyrrolidine with common amino acids using standard peptide chemistry. This series has been compared with the parent compounds for antibacterial activity in vitro and in vivo as well as for comparative solubility. The amino acid analogues were less active in vitro, but had equal or increased efficacy in vivo. Indeed, it was proven that these compounds, which were stable to acid and base under the reaction conditions for their preparation, were rapidly cleaved in serum to give the parent quinolones. The amino acid derivatives showed a 3-70 times improved solubility when compared to the parent compounds. The most active compound of the series was [S- (R*,R*)]-7-[3-[(2-amino-1-oxopropyl)-amino]-1-pyrrolidinyl]-1-cyclopropyl- 6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (PD 131112).