678991-40-7

Basic information

• Product Name: (+)-(1'S,2'S,3S)-3-dibenzylamino-N,4,4-trimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide
• Synonyms: (+)-(1'S,2'S,3S)-3-dibenzylamino-N,4,4-trimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide
• CAS NO: 678991-40-7
• Molecular Weight: 472.671
• Mol File: 678991-40-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-(1'S,2'S,3S)-3-dibenzylamino-N,4,4-trimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1'S,2'S,3S)-3-dibenzylamino-N,4,4-trimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide(678991-40-7)
• EPA Substance Registry System: (+)-(1'S,2'S,3S)-3-dibenzylamino-N,4,4-trimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide(678991-40-7)

Safety Data

• Hazardous Substances Data: 678991-40-7(Hazardous Substances Data)

Upstream product

• 132278-01-4 (E)-4,4-dimethyl-2-pentenoyl chloride 
• 90-82-4 pseudoephedrine 
• 85175-35-5 lithium dibenzylamide 
• 678991-35-0 E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpent-2-enamide 
• 103-49-1 dibenzylamine 

Downstream Products

• 869468-27-9 (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide 
• 869468-31-5 (-)-(3S)-3-((benzyloxycarbonyl)amino)-4,4-dimethylpentanol 

Relevant articles and documents

A general and enantiodivergent method for the asymmetric synthesis of piperidine alkaloids: concise synthesis of (R)-pipecoline, (S)-coniine and other 2-alkylpiperidines

A simple and very efficient protocol for the preparation of highly enantioenriched 2-alkylpiperidines has been set up, which allows the preparation of the final heterocycles with any wanted configuration at the stereogenic center starting from the same starting material. The key step of the synthesis relies on a diastereodivergent aza-Michael reaction protocol using the readily available and cheap reagent (+)-(S,S)-pseudoephedrine as chiral auxiliary.

Asymmetric Synthesis of β-Amino Esters by Aza-Michael Reaction of α,β-Unsaturated Amides Using (S,S)-(+)-Pseudoephedrine as Chiral Auxiliary

Chiral nonracemic β-amino esters were prepared in good yields and enantioselectivities using the diastereo-selective conjugate addition of nitrogen nucleophiles to α,β-unsaturated amides derived from (S,S)-(+)-pseudoephedrine as the key step. In this way, several β-amino amide adducts were prepared using different conjugate acceptors and two different lithium benzylamides as nucleophiles. These adducts were easily converted in only one step, into the final, highly enantioenriched β-amino esters.