49620-06-6

Usage

Uses

Used in Pharmaceutical Research:
(6S,7R)-2-azaspiro[5.5]undecan-7-ol is used as a potential ingredient in the development of drugs for the treatment of various medical conditions. Its unique structure and properties make it a valuable candidate for therapeutic applications.
Used in Chemical Synthesis:
(6S,7R)-2-azaspiro[5.5]undecan-7-ol serves as a building block for the synthesis of a range of other chemical compounds. Its versatile structure allows for the creation of new molecules with potential applications in various industries, including pharmaceuticals, materials science, and more.
Used in Drug Development:
In the pharmaceutical industry, (6S,7R)-2-azaspiro[5.5]undecan-7-ol is used as a key component in the development of new drugs. Its unique properties and potential therapeutic effects make it an attractive candidate for further research and development.
Used in Chiral Chemistry:
The presence of a chiral center in (6S,7R)-2-azaspiro[5.5]undecan-7-ol makes it an important compound in the field of chiral chemistry. It can be used to study the effects of stereochemistry on biological activity and to develop enantiomerically pure compounds with specific therapeutic properties.

Upstream product

• 925422-77-1 1-(toluene-4-sulfonyl)-3-(5-trimethylsilylpent-4-ynyl)piperidin-2-one 
• 66927-74-0 5-bromo-1-(trimethylsilyl)pentyne 
• 851053-91-3 3-formyl-3-(3-oxo-butyl)-piperidine-1-carboxylic acid ethyl ester 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 98721-35-8 1,4-Dioxa-8-aza-dispiro[4.0.5.4]pentadecane 
• 92423-37-5 2-(3-aminopropyl)cyclohexanone ethylene acetal 
• 122419-43-6 (6S,7R)-2,5-Bis-(toluene-4-sulfonyl)-2-aza-spiro[5.5]undecan-7-ol 
• 111467-62-0 2-oxopiperidine-3(S)-spiro-2'-<1(S)-hydroxycyclohexane> 
• 4845-04-9 1-cyclohexene-1-methanol 
• 125993-10-4 (1R,6R)-7-oxabicyclo[4.1.0]heptan-1-ylmethanol 
• 125943-20-6 Trifluoro-methanesulfonic acid (1R,6R)-1-(7-oxa-bicyclo[4.1.0]hept-1-yl)methyl ester 
• 1320327-46-5 (S)-methyl 3-allyl-2-oxo-1,2,3,6-tetrahydropyridine-3-carboxylate 
• 1356215-31-0 (R)-3-allyl-2-oxo-1,2,3,6-tetrahydropyridine-3-carbaldehyde 
• 1356215-35-4 (R)-3-allyl-3-[(R)-1-hydroxybut-3-enyl]-1,6-dihydropyridin-2(3H)-one 

Downstream Products

• 81149-24-8 N-methyl-O-tosylisonitramine 
• 81149-27-1 (S)-8-[1-Phenyl-meth-(E)-ylidene]-2-aza-spiro[5.5]undecan-7-one 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of Nitraria Alkaloids: (+)-Nitramine, (+)-Isonitramine, (-)-Isonitramine, and (-)-Sibirine via Asymmetric Phase-Transfer Catalytic α-Allylations of α-Carboxylactams

Many optically active 2-azaspirocyclic structures have frequently been found in biologically active natural products. In particular, Nitraria alkaloids, (+)-nitramine, (+)-isonitramine, (-)-isonitramine, and (-)-sibirine, have stereogenicity on their quat

Highly enantioselective total synthesis of (+)-isonitramine

A new efficient enantioselective synthetic method of (+)-isonitramine is reported. (+)-Isonitramine was obtained in 12 steps (98% ee and 43% overall yield) from δ-valerolactam via enantioselective phase-transfer catalytic alkylation, Dieckman condensation

Enantioselective total syntheses of (-)-isonitramine, (-)-sibirine, and (+)-nitramine by ring-closing metathesis

Concise enantioselective total syntheses of naturally occurring 2-azaspiro[5,5]undecan-7-ol (Nitraria) alkaloids viz. (-)-isonitramine, (-)-sibirine, and (+)-nitramine are accomplished in 42, 38, and 25 % overall yield, respectively, in six steps starting

Platinum(II)-catalyzed cyclizations forming quaternary carbon centers, using enesulfonamides, enecarbamates, or enamides as nucleophiles

(Chemical Equation Presented) Cyclic enesulfonamides, enecarbamates, or enamides tethered to an alkyne cyclize readily with use of platinum(II) chloride. This reaction generates quaternary-substituted carbon centers within simple spiro-fused or more compl

Hydride-promoted ring expansion of 2-azaspiropyrrolinium salts: An approach towards the synthesis of (-)-nitramine

An enantioselective approach toward the synthesis of the spiroalkaloid (-)-nitramine was achieved by electrophile-induced cyclization of a suitably substituted and protected chiral α-allylcyclohexanecarboxaldimine. Its hydride-promoted ring expansion after spirocyclization gave rise to the competitive formation of isomeric spiropyrrolidines and a spiropiperidine, the latter being further transformed into (-)-nitramine. Georg Thieme Verlag Stuttgart.

Synthesis of racemic nitramine, isonitramine and sibirine

Condensation of enol ether 6 with methyl vinyl ketone led easily to ketoaldehyde 7 whose cyclisation afforded the azaspiranic enone 8, a key intermediate for the synthesis of the title alkaloids.

An asymmetric synthesis of (+)-isonitramine by 'triple allylic strain-controlled' intramolecular S(N)2' alkylation

The spirocyclic alkaloid (+)-isonitramine (1) has been synthesized in a stereoselective manner utilizing a novel 'triple allylic strain-controlled' intramolecular lactam enolate S(N)2' alkylation.

PLE-catalyzed resolution of α-substituted β-ketoesters application to the synthesis of (+)-Nitramine and (-)-Isonitramine

Substituted β-ketoesters can be prepared in enantiomerically pure form by pig liver esterase catalyzed hydrolysis of their racemic precursors. With the asymmetric carbon atom possessing a quaternary centre, (+)-Nitramine and (-)-Isonitramine have been syn

Stereoselective Synthesis of (+/-)-Isonitramine and (+/-)-Sibirine

Spirocyclic alkaloids, (+/-)-isonitramine and (+/-)-sibirine were synthesized in high overall yields via a chemoselective reduction by Hantzsch ester (HEH), a coenzyme NADH model compound.