84839-56-5

Basic information

• Product Name: (1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester
• CAS NO: 84839-56-5
• Molecular Weight: 269.341
• Mol File: 84839-56-5.mol

Chemical Properties

• CAS DataBase Reference: (1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester(84839-56-5)
• EPA Substance Registry System: (1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester(84839-56-5)

Safety Data

• Hazardous Substances Data: 84839-56-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester is utilized as a key building block in organic synthesis, facilitating the creation of diverse chemical compounds. Its unique structure allows for a range of reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester is employed as an intermediate in the preparation of various medicinal compounds. Its ability to undergo selective reactions, due to the Boc protecting group, makes it an advantageous starting material for the development of new drugs.
Used in Drug Discovery and Development:
(1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester is also crucial in drug discovery and development, where its structural attributes can be leveraged to design and synthesize potential therapeutic agents. The Boc group's protective role ensures that the tetrahydropyridine ring can be selectively modified, which is essential for optimizing the pharmacological properties of the resulting drug candidates.
Used in Chemistry and Biology:
(1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester finds applications across various sectors of chemistry and biology, where its unique structure and reactivity contribute to the advancement of scientific research and the development of novel applications.

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 

Relevant articles and documents

Synthesis of piperidine derivatives fused to a tetrahydrofuran ring

Intramolecular nucleophilic opening of the oxirane ring in tert-butyl 6-(2-hydroxyethyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate by the action of excess potassium hydroxide in 75% aqueous dimethyl sulfoxide at 110-120 C gave tert-butyl (3aR,7aS)-3a-hydroxyhexahydrofuro[2,3-c]pyridine-6(2H)- carboxylate whose treatment with POCl3 resulted in elimination of water molecule and tert-butoxycarbonyl group with formation of 2,3,4,5,6,7-hexahydrofuro[2,3-c]pyridine hydrochloride. The latter reacted with electrophiles (acetic anhydride, methanesulfonyl chloride, and benzaldehyde in combination with sodium triacetoxyhydridoborate) in the presence of triethylamine, yielding the corresponding N-substituted 2,3,4,5,6,7- hexahydrofuro[ 2,3-c]pyridine derivatives.

Synthesis of Quinuclidines by Intramolecular Silver-Catalysed Amine Additions to Alkynes

A new method has been developed for the synthesis of 2-alkylidenequinuclidines based on a silver triflate catalysed intramolecular hydroamination of 4-(prop-2-ynyl)piperidines. Monosubstituted piperidines reacted less efficiently than cis-disubstituted piperidines, and the reaction was selective for an alkyne moiety, even in the presence of a vinyl group at the 3-position. The hydroamination occurred readily with a terminal alkyne, as well as with an internal alkyne bearing an aliphatic or aromatic group at the terminal carbon atom. Using this silver-catalysed cyclization, a short procedure was developed for the relay synthesis of the cinchona alkaloids dihydroquinidine and dihydroquinine. We report the synthesis of (enantiomerically pure) 2-alkylidenequinuclidines by an intramolecular hydroamination reaction catalysed by silver triflate. After cyclization to the appropriate quinuclidines, the cinchona alkaloids dihydroquinidine and dihydroquinine were obtained in a two-step procedure.

Synthesis of the selective muscarinic agonist (3R)-3-(6-chloropyrazin-2-yl)-1-azabicyclooctane

The synthesis of the functionally selective muscarinic agonist (3R)-3-(6-chloropyrazin-2-yl)-1-azabicyclooctane is described commencing from readily available 4-piperidone.The key feature of this novel process is the preparation and resolution of a piperidin-4-ylacetic acid, with the advantage that high yields of the pure (S)-enantiomer may be obtained by epimerization of the unwanted enantiomer for further resolution.The reaction sequence is completed by reduction to a chiral 4-hydroxyethylpiperidine and intramolecular N-alkylation to the bicycle 1.