660861-59-6

Basic information

• Product Name: (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one
• Synonyms: (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one
• CAS NO: 660861-59-6
• Molecular Weight: 403.521
• Mol File: 660861-59-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one(660861-59-6)
• EPA Substance Registry System: (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one(660861-59-6)

Safety Data

• Hazardous Substances Data: 660861-59-6(Hazardous Substances Data)

Upstream product

• 660861-45-0 (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one 
• 502897-36-1 (1R,5R)-5,8,8-Trimethyl-2-oxo-3-oxa-bicyclo[3.2.1]octane-1-carbonyl chloride 
• 183850-84-2 5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carboxylic acid 
• 660861-32-5 (1S,5R)-1-[(1,2-dihydroisoquinolin-2-yl)carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one 

Downstream Products

• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Asymmetric synthesis of 1-substituted 1,2,3,4-tetra-hydroisoquinolines by asymmetric electrophilic α-amidoalkylation reactions

An efficient method for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines via chiral N-acyliminium ions is presented. The N-acyl-1,2-dihydroisoquinolines (8) and (9) underwent smooth oxidation reactions with Ph3C+BF4- to give the chiral N-acylisoquinolinium ions (10) and (13), respectively. Stereoselective addition of organomagnesium and organozinc compounds to intermediates (10) and (13) provided the corresponding 1-substituted N-acyl-1,2-dihydroisoquinolines (11/12) and (14/15) in good yields. The diastereoselectivity of these reactions appeared to be dependent on the structure of the N-acyliminium ion intermediates (10) and (13) and on the nature of the trapping reagent with the zinc reagents in general leading to markedly improved stereoselectivities. Pure diastereomers were obtained by preparative HPLC and readily transformed into enantiopure 1-substituted 1,2,3,4-tetrahydroisoquinolines by catalytic hydrogenation and reductive removal of the chiral auxiliary.