124443-68-1

Basic information

• Product Name: N-Boc-Piperidine-4-carboxylic acid methyl ester
• Synonyms: tert-Butyl methyl piperidine-1,4-dicarboxylate;N-Boc-Isonipecotic acid methyl ester;1-(tert-butyl) 4-methyl tetrahydro-1,4(2H)-pyridinedicarboxylate;N-Boc- Piperidine-4-carboxylate;1-Boc-Piperidine-4-carboxylic acid methyl ester;1,4-Piperidinedicarboxylic acid, 1-(1,1-dimethylethyl) 4-methyl ester;Methyl-boc-piperidine-4-carboxylate;Methyl 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylate
• CAS NO: 124443-68-1
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.3
• Product Categories: pharmacetical;Acids and Derivatives;Amines and Anilines
• Mol File: 124443-68-1.mol
• Article Data: 40

Chemical Properties

• Melting Point: 33.0 to 37.0 °C
• Boiling Point: 307.4 °C at 760 mmHg
• Flash Point: 139.7 °
• Appearance: /
• Density: 1.094 g/cm³
• Vapor Pressure: 3.83E-06mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: -2.29±0.40(Predicted)
• CAS DataBase Reference: N-Boc-Piperidine-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-Piperidine-4-carboxylic acid methyl ester(124443-68-1)
• EPA Substance Registry System: N-Boc-Piperidine-4-carboxylic acid methyl ester(124443-68-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 124443-68-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C12H21NO4/c1-8-5-6-13(9(7-8)10(14)15)11(16)17-12(2,3)4/h8-9H,5-7H2,1-4H3,(H,14,15)/p-1

Upstream product

• 7462-86-4 methyl piperidine-4-carboxylate hydrochloride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 67-56-1 methanol 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 498-94-2 isonipecotic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2971-79-1 isonipecotic acid methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 74-88-4 methyl iodide 

Downstream Products

• 124443-69-2 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]carbonyl]-1-piperidinecarboxylic acid,1,1-dimethylethyl ester 
• 287202-48-6 4-(4-but-2-ynyloxybenzenesulfonyl)-piperidine-1,4-dicarboxylic acid tert-butyl ester methyl ester 
• 578021-55-3 1-tert-butyl 4-methyl 4-ethylpiperidine-1,4-dicarboxylate 
• 226398-39-6 1-(tert-butyl) 4-methyl-4-{[4-(4-chlorophenoxy)phenyl]sulfonyl}-1,4-piperidinedicarboxylate 
• 741687-06-9 1-tert-butyl 4-methyl 4-benzylpiperidine-1,4-dicarboxylate 
• 724790-59-4 4-methyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester 
• 885523-41-1 1-boc-4-ethyl-4-formylpiperidine 
• 885500-37-8 4-(4-chlorobenzyl)piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester 
• 1314319-01-1 1-tert-butyl 4-methyl 4-(chloromethyl)piperidine-1,4-dicarboxylate 
• 1312131-45-5 tert-butyl 4-(chloromethyl)-4-(hydroxymethyl)piperidine-1-carboxylate 
• 1314319-14-6 C₂₀H₃₀N₂O₂ 
• 1314319-17-9 C₂₁H₃₀N₂O₄ 
• 1345672-65-2 C₁₈H₂₉BN₂O₄ 
• 1345810-14-1 C₁₈H₂₈BClN₂O₄ 

Relevant articles and documents

Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives

Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs2 molecule. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biological studies. Mechanistic study based on experiments and density functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an SN2 reaction by NTs2 as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asymmetric variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES

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