113965-36-9

Upstream product

• 30880-59-2 5-oxo-octanal 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 627-31-6 1,3-Diiodopropane 
• 2386-64-3 ethylmagnesium chloride 
• 178313-97-8 (S)-N-(1-phenylethyl)-2-methylideneaziridine 
• 912358-37-3 1-[(1S)-phenylethyl]-2-propylpiperidine-2-carbonitrile 
• 111-24-0 1,5-dibromo-pentane 
• 3074-61-1 1-propylcyclopentene 
• 7529-63-7 (1'S)-(-)-1-(1'-phenylethyl)piperidine 
• 912358-35-1 1-[(1S)-1-phenylethyl]piperidine-2-carbonitrile 

Downstream Products

• 458-88-8 coniine 
• 555-92-0 (S)-coniine hydrochloride 

Relevant academic research and scientific papers

Asymmetric synthesis of 2-substituted piperidines using a multi-component coupling reaction: Rapid assembly of (S)-coniine from (S)-1-(1-phenylethyl)-2-methyleneaziridine

(S)-Coniine is made using a reaction which assembles the piperidine ring by the sequential formation of four new chemical bonds and installs the C-2 stereogenic centre with high levels of diastereocontrol (90% de).

Anodic cyanation of (S)-(-)-1-1(1-phenylethyl)piperidine: An expeditious synthesis of (S)-(+)-coniine

A short and efficient asymmetric synthesis of enantiopure (S)-(+)-coniine is reported. Anodic cyanation of (-)-1-[(1S)-1-phenylethyl]piperidine, derived from [(1S)-1-phenylethyl]amine, results in regioselective formation of the corresponding α-amino-nitrile, which was alkylated with propyl iodide to give a bifunctional derivative. The latter underwent a stereoselective reductive decyanation (80% de), the product of which was hydrogenolyzed to afforded (S)-(+)-coniine (99% ee) with an overall 35% yield from (-)-1 -[(1S)-1-phenylethyl]piperidine. Georg Thieme Verlag Stuttgart.

An Asymmetric Synthesis of 2-Substituted Piperidines through Ozonolysis of Cyclopentenes and Reductive Aminocyclization

By the action of ozone, sodium cyanoborohydride and the optically active benzylic amines 2, the 1-substituted cyclopentenes 1, 5 and 9 were converted to a diastereometric mixture of 1,2-disubstituted piperidines (3, 6 and 10), respectively.Hydrogenation of these compounds and the following work-up yielded optically active 2-alkylpiperidines (4, up to 68percente.e.), pipecolic acid (7, 84percent e.e.) and 2-(hydroxymethyl)piperidine (11, up to 85percente.e.).Chromatographic separation of the major isomers of 3b and 6 enabled optically pure coniine (4b) and pipecolic acid (7) to be prepared, respectively.