176239-76-2

Basic information

• Product Name: (S)-N-benzyl-N-(4-methyl-3-pentenyl)alanine butyl ester
• Synonyms: (S)-N-benzyl-N-(4-methyl-3-pentenyl)alanine butyl ester
• CAS NO: 176239-76-2
• Molecular Weight: 317.472
• Mol File: 176239-76-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-N-benzyl-N-(4-methyl-3-pentenyl)alanine butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzyl-N-(4-methyl-3-pentenyl)alanine butyl ester(176239-76-2)
• EPA Substance Registry System: (S)-N-benzyl-N-(4-methyl-3-pentenyl)alanine butyl ester(176239-76-2)

Safety Data

• Hazardous Substances Data: 176239-76-2(Hazardous Substances Data)

Upstream product

• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 2885-02-1 (S)-butyl 2-aminopropanoate 
• 100-39-0 benzyl bromide 
• 176239-72-8 (S)-N-(4-methyl-3-pentenyl)alanine butyl ester 

Downstream Products

• 176239-91-1 (S)-N-benzyl-N-(4-methyl-3-pentenyl)alaninol 
• 176239-97-7 (S)-N-benzyl-N-(4-methyl-3-pentenyl)alaninal 
• 176240-03-2 (S)-N-benzyl-N-(4-methyl-3-pentenyl)alaninal benzylimine 

Relevant articles and documents

Preparation of 2,3,4-trisubstituted piperidines by a formal hetero-ene reaction of amino acid derivatives

N-Benzyl- or N-tosyl-N-(4-methyl-3-pentenyl)amino aldehyde benzylimines, which are obtained from alanine, leucine, or phenylalanine methyl esters in five steps, can be cyclized diastereoselectively in the presence of Lewis acids to give 3-amino-2,4-dialkyl-substituted piperidines. The product distribution and diastereoselectivity depends on the type of Lewis acid and nitrogen-protecting group. Benzyl-protected imines give 2-alkyl-3-(benzylamino)-4-isopropenyl piperidines with FeCl3 and 2-alkyl-3-(benzylideneamino)-4-isopropylpiperidines with TiCl4. Tosyl-protected imines show a decreased level of selectivity. The relative configurations of the piperidines were established by NMR and X-ray crystal structure analyses. Iminium ion cyclization followed by two competitive ionic pathways, i.e. either proton elimination or hydride transfer are discussed for these reactions.