765913-41-5

Basic information

• Product Name: (1R)-(+)-1-phthalimidomethyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 765913-41-5
• Molecular Weight: 292.337
• Mol File: 765913-41-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R)-(+)-1-phthalimidomethyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(+)-1-phthalimidomethyl-1,2,3,4-tetrahydroisoquinoline(765913-41-5)
• EPA Substance Registry System: (1R)-(+)-1-phthalimidomethyl-1,2,3,4-tetrahydroisoquinoline(765913-41-5)

Safety Data

• Hazardous Substances Data: 765913-41-5(Hazardous Substances Data)

Upstream product

• 765913-39-1 2-[(R)-2-((S)-Toluene-4-sulfinyl)-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl]-isoindole-1,3-dione 
• 88422-83-7 2-(3,4-dihydro-1-isoquinolinylmethyl)-1H-isoindole-1,3(2H)-dione 
• 6780-38-7 N-phthaloylglycine chloride 
• 88422-74-6 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(2-phenylethyl)acetamide 
• 64-04-0 phenethylamine 
• 136918-14-4 phthalimide 
• 27328-34-3 2-(2,2-dimethoyxethyl)-1H-isoindole-1,3(2H)-dione 
• 765913-38-0 (S)-4-methyl-N-(2-phenylethyl)benzenesulfinamide 

Downstream Products

• 765915-89-7 N-[(R)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide 
• 135526-78-2 (-)-Praziquantel 

Relevant articles and documents

Enantioselective synthesis of (R)-(-)-praziquantel (PZQ)

Praziquantel 8 (2-cyclohexylcarbonyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline-4-one), a powerful anti-worm drug, has been synthesized in its enantiopure form via asymmetric transfer hydrogenation according to the Noyori protocol. Initially, the reduction of prochiral imine 4 afforded product 5 in 62% ee, but a single crystallization amplified the enantiomeric purity to 98% ee. The final (R)-(-)-praziquantel 8 was prepared in three subsequent steps in 56% chemical yield.

Total synthesis of (-)-praziquantel: An anthelmintic drug

The optically pure (-)-praziquantel was synthesised using phenylethylamine as starting material in 12% overall yield. The key step was achived by a chiral auxiliary mediated Pictet-Spengler reaction.