71785-60-9

Basic information

• Product Name: (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(3-methylpyridyl)-3,6-dihydropyrazin
• Synonyms: (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(3-methylpyridyl)-3,6-dihydropyrazin
• CAS NO: 71785-60-9
• Molecular Weight: 261.324
• Mol File: 71785-60-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(3-methylpyridyl)-3,6-dihydropyrazin(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(3-methylpyridyl)-3,6-dihydropyrazin(71785-60-9)
• EPA Substance Registry System: (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(3-methylpyridyl)-3,6-dihydropyrazin(71785-60-9)

Safety Data

• Hazardous Substances Data: 71785-60-9(Hazardous Substances Data)

Upstream product

• 3099-31-8 nicotinyl chloride 
• 10065-72-2 L-Alanine methyl ester 
• 420-37-1 trimethoxonium tetrafluoroborate 

Downstream Products

• 10065-72-2 L-Alanine methyl ester 
• 71785-66-5 (R)-α-(3-Pyridylmethyl)alanin-methylester 

Relevant articles and documents

Asymmetric Syntheses via Heterocyclic Intermediates, V. - Asymmetric Synthesis of α-Methyl Amino Acids by Alkylation of the Lithiated Lactim Ether of cyclo-(L-Ala-L-Ala)

The (3S,6S)-2,5-dimethoxy-3,6-dimethyl-3,6-dihydropyrazine (7) is obtained from cyclo-(L-Ala-L-Ala) 5 (93-95percent optically pure) and trimethyloxonium tetrafluoroborate.With butyllithium the lithio derivative 8 is formed which reacts with alkyl halides in good chemical yields and with more than 90percent diastereoselectivity, whereby R-configuration is induced at C-3.A model concept is discussed, which explains the remarkably high asymmetric induction. - Hydrolysis (0.25 N HCl, room temp.) gives L-alanine methyl ester (4) and the (R)-α-methyl amino acid methyl esters 13.The two amino acid esters are separable by distillation or chromatography.