673461-23-9

Basic information

• Product Name: (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• Synonyms: (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
• CAS NO: 673461-23-9
• Molecular Weight: 366.46
• Mol File: 673461-23-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(673461-23-9)
• EPA Substance Registry System: (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide(673461-23-9)

Safety Data

• Hazardous Substances Data: 673461-23-9(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 77497-96-2 (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester 
• 77497-97-3 benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt 
• 115962-35-1 (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid 
• 100-46-9 benzylamine 
• 74163-81-8 L-Tic-OH 

Relevant articles and documents

Synthesis and characterization of n-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction

In this paper, the preparation and characterization of eight optically pure N-functionalized (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides is described. The prepared amides and thioamides were tested as organocatalysts of aldol reaction of 4-nitrobenzaldehyde and acetone. The highest ee of formation of 4-hydroxy-4-(4-nitrophenyl)butan-2-one was obtained with (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (77% ee). The observed deceleration of the aldol reaction catalyzed in this way, as compared with that catalyzed with (S)-proline, was attributed to the formation of little reactive cyclic intermediate, which was isolated and characterized.

Optimized synthesis of tetrahydroisoquinoline-hydantoins

Several methods have been developed and compared for the solution synthesis of tetrahydroisoquinoline-hydantoin derivatives. The best yields were obtained when the imidazolidine-2,4-dione ring was synthesized in two steps: (1) reaction of Tic-OH with the appropriate amine and (2) cyclization with 1,1′-carbonyldiimidazole.