208345-53-3

Basic information

• Product Name: (S)-(-)-N,N-diethyl-4-methoxy-2-(2-amino-2-phenylethyl)benzamide
• Synonyms: (S)-(-)-N,N-diethyl-4-methoxy-2-(2-amino-2-phenylethyl)benzamide
• CAS NO: 208345-53-3
• Molecular Weight: 326.439
• Mol File: 208345-53-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-(-)-N,N-diethyl-4-methoxy-2-(2-amino-2-phenylethyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N,N-diethyl-4-methoxy-2-(2-amino-2-phenylethyl)benzamide(208345-53-3)
• EPA Substance Registry System: (S)-(-)-N,N-diethyl-4-methoxy-2-(2-amino-2-phenylethyl)benzamide(208345-53-3)

Safety Data

• Hazardous Substances Data: 208345-53-3(Hazardous Substances Data)

Upstream product

• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 90359-73-2 N,N-diethyl-4-methoxy-2-methylbenzamide 

Downstream Products

• 208345-57-7 (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 
• 208345-58-8 (3R,4S)-(+)-4-(tert-butyldiphenylsilyloxy)-6-methoxy-N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 208345-56-6 (3R,4S)-(+)-4-hydroxy-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 
• 208345-55-5 (3S)-(-)-6-methoxy-N-methyl-3-phenyl-3,4-dihydro-1(2H)-isoquinolone 
• 208345-54-4 (-)-(S)-6-methoxy-3-phenyl-3,4-dihydroisoquinolin-1(2H)-one 

Relevant articles and documents

Asymmetric synthesis of 4-hydroxy-3-phenyltetrahydroisoquinoline derivatives using enantiopure sulfinimines (N-sulfinyl imines)

Addition of lateral lithiated amides and phthalide anions to enantiopure sulfinimines (N-sulfinyl imines) represents a new approach for the asymmetric synthesis of 3-substituted isoquinolones and 3-substituted 4-hydroxy isoquinolones, respectively, important chiral building blocks for isoquinoline alkaloid synthesis. In one example 3-phenylisoquinolone (-)-15b was prepared in >95% ee by treatment of amide ion 10b with sulfinimine (S)- (+)-11 and subsequent deprotection of the N-sulfinyl auxiliary and cyclization. Oxaziridine-mediated hydroxylation of the anion of 16 afforded 4-hydroxy isoquinolone 19, which was transformed into 4-hydroxy-3- phenyltetrahydroisoquinoline (-)-22. In another approach 22 was prepared more directly by addition of phthalide ion 26 to (S)-(+)-11, creating the two stereogenic centers simultaneously. The selectivity proved to be highly counterion dependent.