190774-40-4

Upstream product

• 190774-37-9 (2S,3R,4S)-N-benzyl-3-hydroxy-4-isopropenyl-2-phenylpiperidine 
• 190774-39-1 Methanesulfonic acid (2S,3R,4S)-1-benzyl-4-isopropenyl-2-phenyl-piperidin-3-yl ester 

Relevant academic research and scientific papers

Enantioselective approach towards potential substance P antagonists via hetero-ene reaction of phenylglycine derivatives

Phenylglycine methyl ester 7 can be converted in a four-step sequence to the aldehyde 11. Lewis acid catalyzed hetero-ene reaction of 11 gave a mixture of 3-hydroxy-2-phenylpiperidines 14a,b with high diastereoselectivity. The major diastereomer 14a was further transformed into 4-isopropyl-3-(2-methoxybenzylamino)-2-phenylpiperidine (19), a compound structurally related to a substance P antagonist, in five steps via azide displacement and reductive amination.