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Usage

Uses

Used in Pharmaceutical Industry:
1-N-Boc-2-Ethoxycarbonylmethyl-piperidine is used as a key intermediate in the synthesis of various drugs and bioactive molecules. Its unique structure allows for the development of new synthetic methodologies and the creation of novel chemical entities with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine serves as a building block for the synthesis of biologically active compounds. Its presence in the molecular structure can influence the pharmacological properties of the final product, contributing to the discovery of new drugs with improved efficacy and safety profiles.
Used in Drug Discovery:
1-N-Boc-2-Ethoxycarbonylmethyl-piperidine is utilized in drug discovery processes to explore its potential as a precursor for the development of new pharmaceutical agents. Its reactivity and structural features make it an attractive candidate for the synthesis of compounds with diverse biological activities, expanding the scope of available treatments for various diseases and conditions.

InChI:InChI=1/C14H25NO4/c1-5-18-12(16)10-11-8-6-7-9-15(11)13(17)19-14(2,3)4/h11H,5-10H2,1-4H3

Upstream product

• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 123387-55-3 1-t-butoxycarbonyl-2-tributylstannylpiperidine 
• 2739-99-3 2-ethoxycarbonylmethylpiperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 

Downstream Products

• 170491-61-9 2-(2-oxoethyl)-1-piperidinecarboxylic acid tert-butyl ester 
• 475301-86-1 (-)-sparteine 
• 489-54-3 (1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-8,16-dione 
• 299-39-8 (-)-sparteine; bis-hydrogen sulfate 
• 1000291-89-3 (R)-tert-butyl 2-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate 
• 159898-10-9 (S)-2-{1-[(tert-butoxy)carbonyl]piperidin-2-yl}acetic acid 
• 1410806-66-4 1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-(piperidin-2-yl)ethanone 
• 1410806-65-3 tert-butyl 2-(2-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-oxoethyl)piperidine-1-carboxylate 
• 10248-30-3 lupinine 

Relevant academic research and scientific papers

Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate

α-Trifluoromethyl azocanes are accessible from 2-(trifluoropropan-2-ol) piperidines by metal-free ring-expansion involving a bicyclic azetidinium intermediate. The opening of the azetidinium intermediate was achieved by various nucleophiles (amines, alcoholates, carboxylates, phosphonates, halides and pseudo-halides) with an excellent regio- diastereo- and enantioselectivity and in good yields. The relative configuration of the piperidines and azocanes were assigned and the deprotected azocanes offer opportunities for further derivatization.

Gram-Scale Synthesis of the (?)-Sparteine Surrogate and (?)-Sparteine

An 8-step, gram-scale synthesis of the (?)-sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (?)-sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.

Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C

A concise, efficient and modular approach to the tylophora alkaloids is described, a family of potent cytotoxic agents that are equally effective against drug sensitive and multidrug resistant cancer cell lines. The advantages of the chosen route are illustrated by the total syntheses of the phenanthroquinolizidine cryptopleurine (1) and the phenanthroindolizidines (-)-antofine (2), (-)-tylophorine (3), and their only recently isolated congener (-)-ficuseptine C (4). The key steps consist in a Suzuki cross-coupling between a (commercial) boronic acid and a simple aryl-l,2-dihalide followed by elaboration of the resulting products into the corresponding 2-alkynyl-biphenyl derivatives 27, 33, 41 and 46. The latter undergo PtCl2-catalyzed cycloisomerizations with formation of the functionalized phenanthrenes 28, 34, 42 and 47, which were transformed into the targeted alkaloids by a deprotection/Pictet-Spengler annulation tandem. Due to the flexibility and robust character of this approach, it might enable a systematic exploration of the pharmacological profile of this promising class of bioactive natural products.

Oxidative Generation of N-Acyliminium Ions from N-1-(Tributylstannyl)alkyl Carboxamides and Carbamates and Their Reactions with Carbon Nucleophiles

Oxidation of N-1-(tributylstannyl)alkyl carboxamides and carbamates with ammonium hexanitratocerate (IV) or ferrocenium hexafluorophosphate generates their N-acyliminium ions by the elimination of tributylstannyl radical under mild reaction conditions.The