112496-44-3

Upstream product

• 6612-95-9 (+/-)-3-<6'-(1',4'-dioxaspiro<4.5>decane)>-propanoic acid 
• 4594-78-9 cyclohexanone-2-propionitrile 
• 92423-37-5 2-(3-aminopropyl)cyclohexanone ethylene acetal 
• 78108-84-6 (+/-)-6-(2'-cyanoethyl)-1,4-spiro<4.5>decane 
• 10407-33-7 methyl 3-(2-oxocyclohexyl)propionate 
• 62885-64-7 3-(1,4-dioxaspiro[4.5]dec-6-yl)propionic acid methyl ester 
• 770714-11-9 N-benzyl-3-(1,4-dioxaspiro[4.5]dec-6-yl)propionamide 

Downstream Products

• 111423-98-4 (+/-)-N-benzylnitramine 
• 49620-06-6 (+/-)-isonitramine 
• 111423-98-4 (+/-)-N-benzyl isonitramine 
• 112496-45-4 2-benzyl-2-azaspiro<5.5>undecan-7-one 

Relevant academic research and scientific papers

Angularly substituted octahydroindoles, decahydroquinolines, octahydropyrindines, and octahydrocyclopenta[b]pyrroles by Bruylants reaction

The easily available cycloalkanoyl acetic- and propionic acid esters are transformed to the corresponding amines by standard procedures. These in turn provided an efficient access to cyclic α-aminonitriles, which were reacted with a series of Grignard reagents yielding stereoselectively the cis-configured title compounds; the scope and limitation of this route were investigated. The stereochemical assignment was achieved by X-ray crystallography and NMR spectroscopy. Springer-Verlag 2004.

Synthesis of (+/-)-Nitramine and (+/-)-Isonitramine

The alkaloids (+/-)-nitramine (1; R=H) and (+/-)-isonitramine (2; R=H) have been synthesized, employing an intramolecular Mannich rection to set up the spirocyclic ring system.