516477-38-6

Upstream product

• 33439-27-9 N-tosyl-4-piperidone 
• 98-59-9 p-toluenesulfonyl chloride 
• 80213-12-3 1-[(4-methylbenzene)-sulfonyl]-4-piperidinol 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Downstream Products

• 877614-71-6 3-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carbaldehyde 
• 897625-50-2 4-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-one 
• 877614-78-3 3-(4-fluorophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole 
• 936630-06-7 4-(4-fluorophenyl)-5-(2-methoxyphenyl)-1-(4-methylphenylsulfonyl)-1,2,5,6-tetrahydropyridine 
• 936630-07-8 4-(4-fluorophenyl)-5-(3-methoxyphenyl)-1-(4-methylphenylsulfonyl)-1,2,5,6-tetrahydropyridine 
• 936630-08-9 4-(4-fluorophenyl)-5-(4-methoxyphenyl)-1-(4-methylphenylsulfonyl)-1,2,5,6-tetrahydropyridine 
• 936630-05-6 4-(4-fluorophenyl)-5-(2-methylphenyl)-1-(4-methylphenylsulfonyl)-1,2,5,6-tetrahydropyridine 

Relevant academic research and scientific papers

Synthesis of cis-3,4-diarylpiperidines and cis-3,4-diaryltetrahydropyrans

Substituted cis-3,4-diarylpiperidines and cis-3,4-diaryltetrahydropyrans are synthesized in modest overall yields starting from 4-aryl-1,2,5,6-tetrahydropyridines and 4-aryl-1,2,5,6-tetrahydropyrans via the following sequence: (1) pinacol-type ring contraction having the?combination of m-chloroperoxybenzoic acid and boron trifluoride etherate, (2) Grignard addition with arylmagnesium bromide reagents and followed by boron trifluoride etherate-mediated intramolecular ring-expanded rearrangement, and (3) hydrogenation with hydrogen on 10% palladium-activated carbon. A facile synthesis of 3,4-diarylpyridines was also described by base-induced aromatization.

New synthesis of 3-arylpyrrolines

We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with m-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF 3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6).