849402-63-7

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 160823-80-3 (3aS,3bR,6R,7aR)-2-benzyl-1,2,3a,3b,4,7a-hexahydro-6-phenyl-3,5-dioxa-2,6a-diazacyclopentapentalen-7-one 
• 849402-57-9 (2R,3S,4S)-1-benzyl-4-benzylaminomethyl-3-hydroxy-2-hydroxymethylpyrrolidine 
• 849402-62-6 (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine 

Downstream Products

• 849402-58-0 (3S,4S,5S)-1-benzyl-5-benzylaminomethyl-3,4-dihydroxypiperidine 

Relevant academic research and scientific papers

Stereoselective synthesis of 4-aminomethyl-3-hydroxyprolinols and ring expansion into enantiopure polyfunctionalized piperidines

A stereoselective route was developed to synthesize enantiopure 3,4,5-trisubstituted piperidines in few steps. The functionalities were introduced starting from (S)-pyroglutaminol as chiral material. The method is based on the 1,3-dipolar cycloaddition of N-benzylnitrone to a derived bicyclic α,β-ethylenic lactam, followed by a ring enlargement of five to six membered nitrogen heterocycles through aziridinium ions.