77497-96-2

Basic information

• Product Name: Benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride
• Synonyms: L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;(S)-L-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;(S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;(S)-L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylicacidbenzylesterHCl;Benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride;3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, phenylMethyl ester, (3S)-;(S)-Benzyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate;phenylmethyl ester,(3S)1,2,3,4-tetrahydro-3-Isoquinolinecarboxylic acid
• CAS NO: 77497-96-2
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 303.78
• EINECS: 1533716-785-6
• Product Categories: API intermediates
• Mol File: 77497-96-2.mol

Chemical Properties

• Boiling Point: 411.6 °C at 760 mmHg
• Flash Point: 202.8 °C
• Appearance: /
• Density: 1.159
• Vapor Pressure: 5.5E-07mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Refrigerator
• Solubility: Dimethyl Sulfoxide, Methanol
• CAS DataBase Reference: Benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride(77497-96-2)
• EPA Substance Registry System: Benzyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride(77497-96-2)

Safety Data

• Hazardous Substances Data: 77497-96-2(Hazardous Substances Data)

Usage

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

Upstream product

• 77497-97-3 benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt 
• 74163-81-8 L-Tic-OH 
• 100-51-6 benzyl alcohol 

Downstream Products

• 116174-78-8 benzyl (S)-1,2,3,4-tetrahydro-2-pivaloyl-isoquinoline-3-carboxylate 
• 144564-23-8 benzyl (S)-(-)-1,2,3,4-tetrahydro-2-benzoyl-isoquinoline-3-carboxylate 
• 144564-20-5 benzyl (S)-(-)-1,2,3,4-tetrahydro-2-acetyl-isoquinoline-3-carboxylate 
• 77498-16-9 (S)-2-[(2-Butoxycarbonyl-ethyl)-isopropyl-carbamoyl]-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester 
• 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 

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.

CRYSTALLINE FORM OF QUINAPRIL HYDROCHLORIDE AND PROCESS FOR PREPARING THE SAME

A novel crystalline form of quinapril hydrochloride of formula (I). An amorphous form of quinapril hydrochloride substantially free of impurities, specially diketopiperazine compound, and conforming to pharmacopoeial specifications formed from the said novel crystalline form of quinapril hydrochloride of formula (I). The crystalline quinapril hydrochloride is in the form nitroalkane solvate in which the nitroalkane is nitromethane, nitroethane and nitropropane. Each such nitroalkane solvate having particular characteristic X- ray diffraction patterns. A process for preparation of amorphous from of quinapril hydrochloride, substantially free of impurities, specially diketopiperazine compound, and conforming to pharmacopoeial specifications, using the novel crystalline quinapril hydrochloride as an intermediate. The process involves obtaining free base compound of formula (V) by adjusting the pH of a solution of the benzyl ester maleate salt of quinapril of formula (V) between 7.5-8.5 in a mixture of water and an organic solvent; catalytic hydrogenation of this compound (V) in an alcoholic solvent in the presence of concentrated hydrochloric acid or hydrogen chloride dissolved in an alcoholic solvent and in the presence of catalytic amounts of Pd/C to obtain a residue containing formula (I); crystallization of the said residue by evaporating the alcoholic solvent from a nitroalkane solvent to give crystalline quinapril hydrochloride, associated with a solvate of the nitroalkane solvent, and drying the crystalline quinapril hydrochloride nitroalkane solvate at a temperature between 40°C and 45°C under vacuum to give amorphous quinapril hydrochloride of formula (I).