868157-86-2

Basic information

• Product Name: (3R)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone
• Synonyms: (3R)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone
• CAS NO: 868157-86-2
• Molecular Weight: 371.433
• Mol File: 868157-86-2.mol

Chemical Properties

• CAS DataBase Reference: (3R)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone(868157-86-2)
• EPA Substance Registry System: (3R)-(-)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-3,4-dihydro-1-(2H)-isoquinolone(868157-86-2)

Safety Data

• Hazardous Substances Data: 868157-86-2(Hazardous Substances Data)

Upstream product

• 776301-21-4 (4S)-2,2-dimethyl-3-o-toluoyl-4-benzyloxazolidine 
• 805323-20-0 N-[(1E)-(3,4-dimethoxyphenyl)methylene]-2,2-dimethoxyethanamine 
• 776301-20-3 (4R)-2,2-dimethyl-3-o-toluoyl-4-benzyloxazolidine 

Downstream Products

• 868157-88-4 (R)-(+)-N-(2,2-dimethoxyethyl)-3-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Synthesis of (S)-(-)- and (R)-(+)-O-methylbharatamine using a diastereoselective Pomeranz-Fritsch-Bobbitt methodology

Laterally lithiated (S)-(-)- and (R)-(+)-o-toluamides 6 with a chiral auxiliary derived from (S)- and (R)-phenylalaninol, respectively, were used as the building blocks and chirality inductors in the asymmetric modification of the Pomeranz-Fritsch-Bobbitt synthesis of isoquinoline alkaloids. Their addition to imine 2 proceeded with partial cyclization, giving isoquinolones (+)-7 and (-)-7 along with acyclic products, (-)-8 and (+)-8, respectively. LAH-reduction of (+)-7 and (-)-7, followed by cyclization, afforded both enantiomers of the alkaloid, (S)-(-)- and (R)-(+)-O-methylbharatamine 5, in 32% and 40% overall yield and with 88% and 73% ees, respectively.