74163-81-8

Basic information

• Product Name: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
• Synonyms: (S)-TIC;(S)-N-tert-1,2,3,4-tetrahydroisoquinoline -3-carboxamide;L-1,2,3,4-Tetrahydro;4-Tetrahydro-3-Isoquinolinecarboxylic acid;[S]-1,2,3,4-Tetrahydro-3-Isoquinolingcarboxylic Acid;(S)-1, 2, 3, 4-tetrahydro-3-isoquinolinecarboxylic acid (for Quinapril);(3S)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECA;(S)-1,2,3,4-Tetrahydro-3-isoquinoline-carboxylic acid hydrochloride, 95+%
• CAS NO: 74163-81-8
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: -0
• Product Categories: Quinolines, Isoquinolines & Quinoxalines;IsoquinolinesPeptide Synthesis;Chiral Building Blocks;Heterocyclic Building Blocks;Others;Unnatural Amino Acid Derivatives;Peptide Synthesis;a-amino;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Halogenated Heterocycles ,Thiophenes ,Thiazolines/Thiazolidines;Amino Acids;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;chiral;(intermediate of quinapril);Carboxylic Acids
• Mol File: 74163-81-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 309.12°C (rough estimate)
• Flash Point: 178.8 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1607 (rough estimate)
• Vapor Pressure: 5.62E-07mmHg at 25°C
• Refractive Index: -166 ° (C=1, 1mol/L NaOH)
• Storage Temp.: Store at 0-5°C
• PKA: 2.21±0.20(Predicted)
• BRN: 4842199
• CAS DataBase Reference: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(74163-81-8)
• EPA Substance Registry System: L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid(74163-81-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 74163-81-8(Hazardous Substances Data)

Usage

Description

(S)-(-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is a quinoline derivative, which is used as an intermediate in the synthesis of quinapril. Quinapril, a product developed by Pfizer, was approved by the US FDA in 1991 for the treatment of hypertension, congestive heart failure and angioedema.

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C10H11NO2.ClH/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9;/h1-4,9,11H,5-6H2,(H,12,13);1H/t9-;/m0./s1

Synthetic route

formaldehyd (50-00-0) + L-phenylalanine (63-91-2) → L-Tic-OH (74163-81-8)

Conditions	Yield
With hydrogenchloride In water at 90℃; for 12h; Pictet-Spengler Synthesis;	98%
With hydrogenchloride In water at 90℃; for 12h;	98%
With hydrogenchloride at 85℃; for 9h; Pictet-Spengler condensation;	95%

(-)-menthyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (143767-56-0) → L-Tic-OH (74163-81-8)

Conditions	Yield
With sodium hydroxide In methanol for 6h; Ambient temperature;	94%

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester (77497-96-2) → L-Tic-OH (74163-81-8)

Conditions	Yield
With sodium hydroxide In water for 15h; Ambient temperature;	81%
With hydrogen; palladium on activated charcoal In ethanol; water; acetic acid for 4h; Ambient temperature;	75.4%

(10aS)-3,3-Bis(trifluoromethyl)-1-oxo-(1,2,3,4-tetrahydroisoquinolino)[2,3-c]oxazolidine (367952-43-0) → L-Tic-OH (74163-81-8)

Conditions	Yield
With water In isopropyl alcohol at 20℃;	72%

(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (67123-97-1) → L-Tic-OH (74163-81-8)

Conditions	Yield
With ammonium hydroxide; borane-ammonia complex; recombinant Escherichia coli BL21 (DE3) cells expressed D-amino acid oxidase from Fusarium solani M-0718 In water at 30℃; pH=8; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	68%

(3R,10bS)-3-tert-Butyl-2-methyl-2,3,6,10b-tetrahydro-5H-imidazo[5,1-a]isoquinolin-1-one (123053-49-6) → L-Tic-OH (74163-81-8)

Conditions	Yield
With hydrogenchloride; Dowex 50-WX8; acetic acid In water; toluene at 103℃; for 126h;	67%

(3'S,4R,5S)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone (307304-56-9) → L-Tic-OH (74163-81-8) + (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (103733-65-9)

Conditions	Yield
With water for 12h; Hydrolysis; epimerization; Heating; Title compound not separated from byproducts.;

ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate (15912-55-7, 41234-43-9, 55857-63-1) → L-Tic-OH (74163-81-8)

Conditions	Yield
With chicken liver acetone; water pH=7.5;

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (57060-86-3) → L-Tic-OH (74163-81-8)

Conditions	Yield
With chicken liver acetone; water for 2h; pH=7.5;

(+/-)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid butyl ester → L-Tic-OH (74163-81-8)

Conditions	Yield
With chicken liver acetone; water pH=7.5;

α,α'-dibromo-o-xylene (91-13-4) + chiral Ni complex of Schiff base of glycine and BPB → L-Tic-OH (74163-81-8)

Conditions	Yield
Stage #1: α,α'-dibromo-o-xylene; chiral Ni complex of Schiff base of glycine and BPB With sodium hydroxide In acetonitrile at 20℃; for 0.666667h; Stage #2: In hydrogenchloride; methanol at 50℃; for 0.333333h; Stage #3: In ammonium hydroxide

L-phenylalanine (63-91-2) + Gly-NH-Rink-resinEt halide → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / dimethylsulfoxide 2: 65 percent / SOCl2 3: BF3*OEt2 / 20 °C 4: 72 percent / H2O / propan-2-ol / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 91 percent / dimethylsulfoxide 2: 82 percent / TFA / CHCl3 / 0.5 h 3: 72 percent / H2O / propan-2-ol / 20 °C View Scheme

(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one (150582-52-8) → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / SOCl2 2: BF3*OEt2 / 20 °C 3: 72 percent / H2O / propan-2-ol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 82 percent / TFA / CHCl3 / 0.5 h 2: 72 percent / H2O / propan-2-ol / 20 °C View Scheme

(4S)-4-Benzyl-2,2-bis(trifluoromethyl)-3-chloromethyl-1,3-oxazolidin-5-one (367952-46-3) → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: BF3*OEt2 / 20 °C 2: 72 percent / H2O / propan-2-ol / 20 °C View Scheme

(+/-)-2-acetyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (143767-54-8) → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / 6 N aq. HCl / 4 h / Heating 2: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 3: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme

o-Xylylene dichloride (612-12-4) → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOMe / 4 h / Heating 2: 6 N aq. HCl / 4 h / Heating 3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 4: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: NaOMe / 4 h / Heating 2: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1 3: 86 percent / 6 N aq. HCl / 4 h / Heating 4: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 5: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme

dimethyl 2-acetyl-1,2,3,4-tetrahydro-3,3-isoquinolinedicarboxylate (143767-55-9) → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 6 N aq. HCl / 4 h / Heating 2: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 3: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1 2: 86 percent / 6 N aq. HCl / 4 h / Heating 3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 4: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme

α,α'-dibromo-o-xylene (91-13-4) + sodium-compound of (+-)-acetylamino-cyano-acetic acid ethyl ester → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 75 percent / NaOMe / 4 h / Heating 2: 6 N aq. HCl / 4 h / Heating 3: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 4: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 75 percent / NaOMe / 4 h / Heating 2: 1.) KOH, 2.) 2 N HCl / 1.) MeOH, H2O, reflux, 4 h, 2.) EtOAc, pH 1 3: 86 percent / 6 N aq. HCl / 4 h / Heating 4: 83 percent / p-TsOH*H2O / toluene / 30 h / Heating 5: 94 percent / NaOH / methanol / 6 h / Ambient temperature View Scheme

Phenylalanine (150-30-1) + α-ureido-β-phenyl-propionic acid → L-Tic-OH (74163-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / conc. HCl View Scheme

formaldehyd (50-00-0) + aqueous NH4OH + L-phenylalanine (63-91-2) + sulfuric acid (7664-93-9) → L-Tic-OH (74163-81-8)

Conditions	Yield
In hydrogenchloride; ethanol; water

formaldehyd (50-00-0) + 2-methyl-3-phenylpropionic acid (1009-67-2, 5628-72-8, 14367-54-5, 14367-67-0) → L-Tic-OH (74163-81-8)

Conditions	Yield
With hydrogenchloride; water Reflux;

methanol (67-56-1) + L-Tic-OH (74163-81-8) → methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate (79815-19-3)

Conditions	Yield
With thionyl chloride	100%
With thionyl chloride at 0 - 20℃;	96%
With sulfuric acid for 12h; Reflux;	95%

chloroformic acid ethyl ester (541-41-3) + L-Tic-OH (74163-81-8) → 2-carboethoxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (104882-53-3)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water 1.) 0 deg C to room temperature, 2.) room temperature, 3 h;	100%

di-tert-butyl dicarbonate (24424-99-5) + L-Tic-OH (74163-81-8) → (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid (115962-35-1, 144069-68-1, 78879-20-6)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h;	100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; Time;	100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 144h; Concentration;	100%

methanol (67-56-1) + L-Tic-OH (74163-81-8) → (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride (78183-55-8)

Conditions	Yield
With thionyl chloride	100%
With thionyl chloride at 0 - 40℃; for 21h; Inert atmosphere;	99%
With thionyl chloride at 0 - 40℃; for 21h; Inert atmosphere;	99%
With chloro-trimethyl-silane at 70℃; for 2h; Reflux;

L-Tic-OH (74163-81-8) + benzyl chloroformate (501-53-1) → (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester (79261-58-8)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 16h;	99%
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 16.5h;	99%
With sodium hydrogencarbonate In water at 20℃; for 1.5h;	97%

L-Tic-OH (74163-81-8) → (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (18881-17-9, 62855-02-1, 62928-94-3, 63006-93-9)

Conditions	Yield
With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran for 6h; Reduction; Heating;	96%
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Heating;	86%
With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran	78%

phosgene (75-44-5) + L-Tic-OH (74163-81-8) → (10aS)-10,10a-dihydro[1,3]oxazolo[3,4-b]isoquinoline-1,3,(5H)-dione (186606-17-7)

Conditions	Yield
In tetrahydrofuran; dichloromethane at -30 - 20℃;	95%

L-Tic-OH (74163-81-8) → (S)-7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (77141-07-2)

Conditions	Yield
With sulfuric acid; nitric acid at -20℃; for 0.5h;	93%
With sulfuric acid; nitric acid at -10℃; for 3.5h;	90%
With sulfuric acid; potassium nitrate at 5 - 20℃;

formaldehyd (50-00-0) + L-Tic-OH (74163-81-8) → (S)-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions	Yield
With formic acid for 4h; Reflux;	93%

formaldehyd (50-00-0) + L-Tic-OH (74163-81-8) → (S)-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Conditions	Yield
Stage #1: formaldehyd; L-Tic-OH With formic acid In water for 4h; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice;	93%

ethanol (64-17-5) + L-Tic-OH (74163-81-8) → ethyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (15912-55-7)

Conditions	Yield
With thionyl chloride Reflux;	91%
With thionyl chloride
With sulfuric acid at 80℃; for 20h; Inert atmosphere;

trimethylsilyl cyanide (7677-24-9) + benzaldehyde (100-52-7) + L-Tic-OH (74163-81-8) → 2-benzyl-1,2,3,4-tetrahydroisoquinoline-3-carbonitrile (1346425-09-9)

Conditions	Yield
In butan-1-ol at 200℃; for 0.166667h; decarboxylative Strecker reaction; Microwave irradiation; enantioselective reaction;	91%

Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Asn-OH (71989-16-7) + Fmoc-L-Arg-OH (91000-69-0) + L-Tic-OH (74163-81-8) + trifluoroacetic acid (76-05-1) → C46H69N15O8*C2HF3O2

Conditions	Yield
Stage #1: Fmoc-Asn-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 2h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: Fmoc-Leu-OH; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-L-Arg-OH; L-Tic-OH; trifluoroacetic acid Further stages;	89%

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] (12354-84-6, 12354-85-7) + L-Tic-OH (74163-81-8) → chloro-pentamethylcyclopentadienyltetrahydroisoquinolinecarboxylato-iridium

Conditions	Yield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of iridium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, concn., addn. of Et2O, filtration, washing with Et2O, pentane, drying in vac.; elem. anal.;	85%

copper(II) acetate monohydrate (6046-93-1) + L-Tic-OH (74163-81-8) → bis(tetrahydroisoquinolinecarboxylato)copper

Conditions	Yield
In methanol (Ar); addn. of ligand to a soln. of copper salt in methanol; isolation, washing with methanol, ether, drying in vac.; elem. anal.;	84%

L-Tic-OH (74163-81-8) + butan-1-ol (71-36-3) → butyl (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Conditions	Yield
With thionyl chloride at 120℃; for 16h; Inert atmosphere;	84%

L-Tic-OH (74163-81-8) + N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine (877932-98-4) + L-alanine acid chloride (129178-93-4) → quinapril (85441-61-8)

Conditions	Yield
With benzenesulfonamide; phosphorus pentachloride; triethylamine In n-heptane; dichloromethane; water	83.9%

L-Tic-OH (74163-81-8) → isoquinoline-3-carboxylic acid (6624-49-3)

Conditions	Yield
With potassium permanganate In N,N-dimethyl-formamide at 0 - 20℃; for 100.5h; Inert atmosphere;	83%
With potassium permanganate	83%
With potassium permanganate In N,N-dimethyl-formamide at 20℃; for 72h; Cooling with ice;	62%

palladium diacetate (3375-31-3) + L-Tic-OH (74163-81-8) → bis(tetrahydroisoquinolinecarboxylato)palladium

Conditions	Yield
In methanol (Ar); addn. of ligand to a soln. of copper salt in methanol; isolation, washing with methanol, ether, drying in vac.; elem. anal.;	81%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + L-Tic-OH (74163-81-8) → (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid (115962-35-1, 144069-68-1, 78879-20-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h; pH=10;	80%

(Z)-9-octadecenoyl chloride (112-77-6) + L-Tic-OH (74163-81-8) → (S)-2-oleoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions	Yield
With potassium carbonate In water; acetone at 0 - 20℃;	78%

glycolaldehyde dimer (23147-58-2, 110822-84-9, 110822-85-0) + tert-butylisonitrile (119072-55-8, 7188-38-7) + L-Tic-OH (74163-81-8) → 1-oxo-1,3,4,9,9a,10-hexahydro-2-oxa-4a-aza-anthracene-4-carboxylic acid tert-butylamide

Conditions	Yield
In 2,2,2-trifluoroethanol at -40 - 20℃; for 12h; Ugi reaction;	77%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + L-Tic-OH (74163-81-8) → chloro-p-cymenetetrahydroisoquinolinecarboxylato-ruthenium

Conditions	Yield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of ruthenium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration through celite, concn., addn. to pentane, filtration, washing with pentane, drying in vac.; elem. anal.;	77%

trans-di-μ-chloro-dichlorobis(triethylphosphine)diplatinum (15692-96-3) + L-Tic-OH (74163-81-8) → chloro-triethylphosphanetetrahydroisoquinolinecarboxylato-platinum

Conditions	Yield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of platinum complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, addn. of pentane, washing withpentane, drying in vac.; elem. anal.;	77%

dichlorobis(triethylphosphine)-μ-dichlorodipalladium(II) + L-Tic-OH (74163-81-8) → chloro-triethylphosphanetetrahydroisoquinolinecarboxylato-palladium

Conditions	Yield
With CH3ONa In methanol; dichloromethane (Ar); addn. of a soln. of MeONa to a soln. of ligand in methanol, addn. to a soln. of palladium complex in CH2Cl2, stirring for 3 h; evapn., dissolving in CH2Cl2, filtration, evapn., addn. of pentane, cooling to -20°C, washing with pentane, drying in vac.; elem. anal.;	76%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-Tic-OH (74163-81-8) → (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester (79261-58-8)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; for 27h;	74.7%

Upstream product

• 50-00-0 formaldehyd 
• 63-91-2 L-phenylalanine 
• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 15912-55-7 ethyl 1,2,3,4-tetrahydroisoquinoline-3-(S)-carboxylate 
• 7664-93-9 sulfuric acid 
• 64-18-6 formic acid 
• 1009-67-2 2-methyl-3-phenylpropionic acid 
• 91-13-4 α,α'-dibromo-o-xylene 
• 143767-55-9 dimethyl 2-acetyl-1,2,3,4-tetrahydroisoquinoline-3,3-dicarboxylate 
• 612-12-4 o-Xylylene dichloride 
• 143767-54-8 (R,S)-2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 150582-52-8 (4S)-4-Benzyl-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one 
• 57060-86-3 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 367952-43-0 (10aS)-3,3-Bis(trifluoromethyl)-1-oxo-(1,2,3,4-tetrahydroisoquinolino)[2,3-c]oxazolidine 

Downstream Products

• 77497-74-6 (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester 
• 18881-17-9 (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline 
• 79261-58-8 (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester 
• 115962-35-1 (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid 
• 77141-07-2 (S)-7-nitro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 186606-17-7 (10aS)-10,10a-dihydro[1,3]oxazolo[3,4-b]isoquinoline-1,3(5H)-dione 
• 361347-52-6 (S)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid (1-benzyl-piperidin-4-yl)-amide 
• 134732-98-2 (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 393837-14-4 methyl (3S)-2-[(benzylamino)carbonyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 
• 501355-25-5 (S)-N-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 673461-23-9 (S)-N-benzyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 673461-28-4 (S)-N-phenyl-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 

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PROBLEM TO BE SOLVED: To provide a novel nitrogen-containing compound having luminescence property. SOLUTION: A nitrogen-containing compound represented by the following formula (I) in which RA, RB, R1, R2, R3, R4, and X are either one of the following (1) and (2). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)-enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, respectively) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-?-carbolines. (Figure presented.).

Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance

Multifunctional isoquinoline-oxazolines (MIQOXs) were conceived and synthesized from commercially available chiral amino acids. The multifunctional role of MIQOXs was demonstrated by Pd-catalyzed highly enantioselective addition of arylboronic acids to nitrostyrenes, and by the discovery of novel antifungal candidates.