765915-89-7

Basic information

• Product Name: N-[(R)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide
• Synonyms: N-[(R)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide
• CAS NO: 765915-89-7
• Molecular Weight: 272.39
• Mol File: 765915-89-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-[(R)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(R)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide(765915-89-7)
• EPA Substance Registry System: N-[(R)-1-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide(765915-89-7)

Safety Data

• Hazardous Substances Data: 765915-89-7(Hazardous Substances Data)

Upstream product

• 2719-27-9 cyclohexanylcarbonyl chloride 
• 60567-64-8 (1R)-(-)-1-aminomethyl-1,2,3,4-tetrahydroisoquinoline 
• 151004-93-2 (R)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 151004-96-5 (1R)-2-[(tert-butyl) oxycarbonyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 954239-58-8 (1R)-1-hydroxymethyl-2-[(tert-butyl) oxycarbonyl]-1,2,3,4-tetrahydroisoquinoline 
• 41034-52-0 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 40615-08-5 [(isoquinolin-1-yl)methyl]amine 
• 1198-30-7 1-isoquinolinecarbonitrile 
• 79848-93-4 N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide 
• 60567-40-0 N-((1,2,3,4-tetrahydro-1-isoquinolinyl)methyl)acetamide 
• 850130-96-0 2-(4-methoxyphenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline 
• 78317-83-6 2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1447933-70-1 1-(R)-(N-cyclohexylcarboxamidomethyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 135526-78-2 (-)-Praziquantel 

Relevant articles and documents

METHOD FOR THE PRODUCTION OF PRAZIQUANTEL AND PRECURSORS THEREOF

The present invention provides methods of preparing Praziquantel, in particular (R)-Praziquantel and analogues thereof in a stereoselective manner. One method involves asymmetric hydrogenation of the following intermediate compound (I) and subsequent cyclization.

METHOD FOR THE PRODUCTION OF PRAZIQUANTEL AND PRECURSORS THEREOF

The present invention relates to methods for the production of enantiopure or enantioenriched Praziquantel precursors and to methods for the production of enantiopure or enantioenriched Praziquantel comprising the methods for the production of the Praziquantel precursors. The present invention further relates to compounds or intermediates useful in such methods.

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.