118667-62-2

Basic information

• Product Name: 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine
• Synonyms: 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine;REF DUPL: 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine;Ethyl N-Boc-2-piperidineacetate;1-[(1,1-dimethylethoxy)carbonyl]-2-Piperidineacetic acid ethyl ester;tert-Butyl 2-(2-ethoxy-2-oxoethyl)
• CAS NO: 118667-62-2
• Molecular Formula: C₁₄H₂₅NO₄
• Molecular Weight: 271.354
• Mol File: 118667-62-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 339.181°C at 760 mmHg
• Flash Point: 158.931°C
• Appearance: /
• Density: 1.049g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.467
• PKA: -2.00±0.40(Predicted)
• CAS DataBase Reference: 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine(118667-62-2)
• EPA Substance Registry System: 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine(118667-62-2)

Safety Data

• Hazardous Substances Data: 118667-62-2(Hazardous Substances Data)

Usage

General Description

1-N-Boc-2-Ethoxycarbonylmethyl-piperidine is a chemical compound with the molecular formula C16H29NO4. It is a derivative of piperidine with a Boc (tert-butoxycarbonyl) protecting group on the nitrogen atom and an ethoxycarbonylmethyl group on the 2-position. 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine is commonly used as an intermediate in organic synthesis, particularly in the pharmaceutical industry for the production of various drugs and bioactive molecules. Due to its high reactivity and versatility, 1-N-Boc-2-Ethoxycarbonylmethyl-piperidine is valuable in the development of new synthetic methodologies and the creation of novel chemical entities. Additionally, it has potential applications in medicinal chemistry and drug discovery as a building block for the synthesis of biologically active compounds.

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 
• 10248-30-3 lupinine 
• 1410806-65-3 tert-butyl 2-(2-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-oxoethyl)piperidine-1-carboxylate 
• 1410806-66-4 1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-(piperidin-2-yl)ethanone 
• 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 

Relevant articles and documents

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.

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.