211619-94-2

Basic information

• Product Name: methyl (S)-3-(2-bromo-4,5-dimethoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate
• Synonyms: methyl (S)-3-(2-bromo-4,5-dimethoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate
• CAS NO: 211619-94-2
• Molecular Weight: 418.285
• Mol File: 211619-94-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (S)-3-(2-bromo-4,5-dimethoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-3-(2-bromo-4,5-dimethoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate(211619-94-2)
• EPA Substance Registry System: methyl (S)-3-(2-bromo-4,5-dimethoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate(211619-94-2)

Safety Data

• Hazardous Substances Data: 211619-94-2(Hazardous Substances Data)

Upstream product

• 138908-56-2 (S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester 
• 186581-53-3 diazomethane 
• 211619-93-1 (S)-N-(tert-butyloxycarbonyl)-2-bromo-4,5-dihydroxyphenylalaninemethyl ester 

Downstream Products

• 190511-34-3 (S)-3-(2-Bromo-4,5-dimethoxy-phenyl)-2-(5-ethyl-4-oxo-3,4-dihydro-2H-pyridin-1-yl)-propionic acid methyl ester 
• 190517-66-9 methyl (S)-2-amino-3-(2-bromo-4,5-dimethoxyphenyl)propanoate 

Relevant articles and documents

Diastereospecific Synthesis of Tetrahydroisoquinolines via Radical Cyclization: Application in the Synthesis of ent-Tadalafil

An enantioselective synthesis of 1-substituted tetrahydroisoquinolines from L–Dopa methyl ester through intramolecular aryl radical cyclization is demonstrated. The strategy consists of bromination of (S)-2-amino-3-(2-bromo-4,5-dimethoxyphenyl)propanoate followed by condensation with various aldehydes to afford bromoimidate ester. Aryl radicals generated from bromoimidate ester under the radical generating conditions (nBu3SnH/AIBN) cyclizes via 6-endo mode to afford cis-1-substituted tetrahydroisoquinolines exclusively in 99% ee. The utility of this synthetic protocol is demonstrated in the synthesis of (6S, 12aS) Tadalafil (5 steps, 21%, 99% ee). (Figure presented.).

Construction of the tricyclic benzoquinolizine ring system by combination of a tandem Mannich-Michael reaction with a Heck reaction

Tetrahydro- and hexahydrobenzo[a]quinolizinones can be built up efficiently by means of a two step reaction sequence consisting of a tandem Mannich-Michael reaction and a Heck reaction.