77497-97-3

Basic information

• Product Name: Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt
• Synonyms: (S)-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID BENZYL ESTER;(S)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID,PHENYLMETHYL ESTER;(S)-3-benzyloxycarbonyl-1,2,3,4-tetrahydroisoquinolinium p-toluenesulfonate;benzyl (S)-(-)-1,2,3,4-tetrahydroiso-quinolinecar;Benzyl-(S)-1,2,3,4-Tetrahydro-iso-Quinoline-3-Carboxylate;(S)-(-)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid benzyl ester p-toluenesulfonic acid salt;BENZYL (S)-(-)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLATE P-TOLUENESULFONIC ACID;Benzyl-(S)-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylate P-Tosylate
• CAS NO: 77497-97-3
• Molecular Formula: C₇H₈O₃S*C₁₇H₁₇NO₂
• Molecular Weight: 439.53
• EINECS: 406-960-0
• Product Categories: Pharmaceutical Intermediates;Chiral Building Blocks;Heterocyclic Building Blocks;Isoquinolines
• Mol File: 77497-97-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 145-150°C
• Boiling Point: 634.1 °C at 760 mmHg
• Flash Point: 337.3 °C
• Appearance: white crystalline
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt(77497-97-3)
• EPA Substance Registry System: Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt(77497-97-3)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61
• RIDADR: UN 3077
• WGK Germany: 2
• Hazardous Substances Data: 77497-97-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 77497-97-3 differently. You can refer to the following data:
1. Quinapril intermediate
2. Used to prepare a novel class of antifungal agents.

InChI:InChI=1/C17H17NO2.C7H8O3S/c19-17(20-12-13-6-2-1-3-7-13)16-10-14-8-4-5-9-15(14)11-18-16;1-6-2-4-7(5-3-6)11(8,9)10/h1-9,16,18H,10-12H2;2-5H,1H3,(H,8,9,10)/t16-;/m0./s1

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 74163-81-8 L-Tic-OH 
• 100-51-6 benzyl alcohol 
• 77497-95-1 (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 63-91-2 L-phenylalanine 
• 6192-52-5 p-toluenesulfonic acid monohydrate 

Downstream Products

• 134732-98-2 (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 501355-25-5 (S)-N-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1636138-31-2 (S)-N-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1238365-87-1 (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1238365-88-2 (S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1636138-33-4 (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide 
• 1636138-35-6 (S)-N-[(1S)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide 
• 1636138-39-0 (5S)-3(4-nitrophenyl)-2-[(1R)-(1-phenylethyl)]-2,3,10,10a-tetrahydro-5H-imidazo[1,5-b]isoquinoline-1-thione 
• 673461-28-4 (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1636138-41-4 (5S)-3,3-dimethyl-2-[(1R)-(1-phenylethyl)]-2,3,10,10a-tetrahydro-5H-imidazo[1,5-b]isoquinoline-1-thione 
• 115962-35-1 (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid 
• 673461-23-9 (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1636138-19-6 (S)-N-[(4-methylphenyl)sulfonyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 1636138-21-0 (S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 

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.

Facile preparation of optically pure (3S)- and (3R)- 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

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