175463-34-0

Basic information

• Product Name: 4-BOC-AMINOMETHYL-3-HYDROXY-1-N-BOC-PYRROLIDINE
• Synonyms: tert-butyl 3-[2-(tert-butoxy)-2-oxoethyl]-4-hydroxypyrrolidine-1-carboxylate;tert-Butyl 3-(((tert-butoxycarbonyl)aMino)Methyl)-4-hydroxypyrrolidine-1-carboxylate;4-Boc-aMinoMethyl-3-hydroxy-1-Boc-pyrrolidine;1-Pyrrolidinecarboxylic acid, 3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-hydroxy-, 1,1-dimethylethyl ester
• CAS NO: 175463-34-0
• Molecular Formula: C15H28N2O5
• Molecular Weight: 316.395
• Mol File: 175463-34-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 437.1°Cat760mmHg
• Flash Point: 218.2°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.78E-09mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-BOC-AMINOMETHYL-3-HYDROXY-1-N-BOC-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BOC-AMINOMETHYL-3-HYDROXY-1-N-BOC-PYRROLIDINE(175463-34-0)
• EPA Substance Registry System: 4-BOC-AMINOMETHYL-3-HYDROXY-1-N-BOC-PYRROLIDINE(175463-34-0)

Safety Data

• Hazardous Substances Data: 175463-34-0(Hazardous Substances Data)

Usage

General Description

4-BOC-AMINOMETHYL-3-HYDROXY-1-N-BOC-PYRROLIDINE is a chemical compound with the molecular formula C13H24N2O4. It is a derivative of pyrrolidine and contains both a BOC (tert-butoxycarbonyl) protecting group and a hydroxy group. 4-BOC-AMINOMETHYL-3-HYDROXY-1-N-BOC-PYRROLIDINE is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals and bioactive molecules. It is also utilized in the production of N-Boc-protected amino acids, which are important intermediates in peptide synthesis. The presence of the BOC protecting group allows for selective functionalization of the amine group in subsequent reactions, making it a valuable precursor in organic chemistry.

InChI:InChI=1/C15H28N2O5/c1-14(2,3)21-12(19)16-7-10-8-17(9-11(10)18)13(20)22-15(4,5)6/h10-11,18H,7-9H2,1-6H3,(H,16,19)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 773826-73-6 tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate 
• 44981-94-4 N-cyanoethyl glycine ethyl ester 
• 197143-33-2 tert-butyl 3-cyano-4-hydroxypyrrolidine-1-carboxylate 
• 175463-32-8 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 266353-18-8 N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester 

Downstream Products

• 175463-14-6 gemifloxacin 

Relevant articles and documents

Gemifloxacin intermediate preparation method

The invention relates to medicine and related fields, and especially relates to a gemifloxacin intermediate preparation method. According to the invention, acrylonitrile and ethyl glycinate hydrochloride are adopted as initial raw materials; through the processes of a nucleophilic addition reaction, amino protection, condensation, reduction protection, oxidation, oximation and deprotection, the gemifloxacin branched-chain intermediate 4-aminomethylpyrrolidin-3-one-O-methyloxime dihydrochloride is obtained. The route is simple; two steps of reactions are eliminated; raw materials are cheap and easy to obtain; and product yield is high. The route does not need column chromatography separation. The method provides a feasible synthesis route for industrial production.

Novel fluoroquinolone antibacterial agents containing oxime-substituted (Aminomethyl)pyrrolidines: Synthesis and antibacterial activity of 7-(4- (Aminomethyl)-3-(methoxyimino) pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4- oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid (LB20304)

New pyrrolidine derivatives, which bear an alkyloxime substituent in the 4-position and an aminomethyl substituent in the 3-position of the pyrrolidine ring, have been synthesized and coupled with various quinolinecarboxylic acids to produce a series of new fluoroquinolone antibacterials. These fluoroquinolones were found to possess potent antimicrobial activity against both Gram-negative and Gram-positive organisms, including methicillin resistant Staphylococcus aureus (MRSA). Variations at the C-8 position of the quinolone nucleus included fluorine, chlorine, nitrogen, methoxy, and hydrogen atom substitution. The activity imparted to the substituted quinolone nucleus by the C-8 substituent was in the order F (C5-NH2) > F (C5-H) > naphthyridine > Cl = OMe = H against Gram-positive organisms. In the case of Gram-negative strains, activity was in the order F (C5-NH2) > naphthyridine = F (C5-H) > H > Cl > OMe. The advantages provided by the newly introduced oxime group of the quinolones were clearly demonstrated by their comparison to a desoximino compound 30. In addition, the oxime moiety greatly improved the pharmacokinetic parameters of the novel quinolones. Among these compounds, compound 20 (LB20304) showed the best in vive efficacy and pharmacokinetic profile in animals, as well as good physical properties. The MICs (μg/mL) of LB20304, compound 30, and ciprofloxacin against several test organisms are as follows: S. aureus 6538p (0.008, 0.031, and 0.13), methicillin resistant S. aureus 241 (4, 16, and 128), Streptococcus epidermidis 887E (0.008, 0.016, and 0.13), methicillin resistant S. epidermidis 178 (4, 32, and 128), Enterococcus faecalis 29212 (0.063, 0.13, and 1), Pseudomonas aeruginosa 1912E (0.25, 0.5, and 0.13), Escherichia coli 3190Y (0.008, 0.016, and 0.008), Enterobacter cloacae P99 (0.008, 0.031, and 0.008), Actinobacter calcoaceticus 15473 (0.063, 0.13, and 0.25). On the basis of these promising results, LB20304 was selected as a candidate for further evaluation.