127983-46-4

Upstream product

• 100-42-5 styrene 
• 127983-45-3 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine 
• 4801-58-5 N-hydroxypiperidine 
• 70546-85-9 2-phenyl-3,3a,4,5,6,7-hexahydro-2H-isoxazolo<2,3-a>pyridine 
• 109-05-7 2-Methylpiperidin 
• 495-47-6 2-(2'-hydroxy-2'-phenylethyl)piperidine 
• 34418-91-2 2,3,4,5-tetrahydropyridine N-oxide 
• 55386-67-9 2-methyl-3,4,5,6-tetrahydropyridine-1-oxide 

Downstream Products

• 131697-74-0 (2S,3aR)-8-Benzyl-3a-methyl-2-phenyl-hexahydro-isoxazolo[2,3-a]pyridin-8-ium; bromide 

Relevant academic research and scientific papers

Nitrone Cycloadditions: Synthesis of (+/-)-Andrachamine

The usefulness of the cycloaddition of alkenes to 2-alkyl-2,3,4,5-tetrahydropyridine oxides for the preparation of trans-2,6-dialkylpiperidines is confirmed by a stereoselective synthesis of (+/-)-andrachamine.Peroxy acid oxidation of 9-oxa-1-azabicyclononanes does not lead regioselectively to the corresponding 2-alkyl-2,3,4,5-tetrahydropyridine oxide, as had previously been claimed.

Nitrone Cycloaddition: Peroxy Acid Oxidation of 2-Phenyl-1-oxa-9-azabicyclononane

Oxidation of 2-phenyl-1-oxa-9-azabicyclononane (5) with m-chloroperoxybenzoic acid is not regioselective, in contrast to the case with the corresponding 1-oxa-8-azabicyclooctane (2; n = 1, R1 = H, R2 = Ph), affording mainly the keto-nitrone (7).On reaction with styrene in boiling toluene the latter forms the oxabicyclononane (9).