79815-20-6

Basic information

• Product Name: (S)-(-)-Indoline-2-carboxylic acid
• Synonyms: (R)-1H-INDOLE-2-CARBOXYLIC ACID;(R)-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID;(R)-(+)-2,3-DIHYDROINDOLE-2-CARBOXYLIC ACID;Perindopril Intermediate;(2S)-indoline-2-carboxylic acid;(2S)-2,3-dihydro-1H-Indole-2-carboxylic acid;(S)-(-)-Indoline-2-CarboxylicAcid98%;S-(-)-Oindolium-2-CarboxylicAcid
• CAS NO: 79815-20-6
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 410-860-2
• Product Categories: PYRROLE;Indoles and derivatives;pharmacetical;chiral;PERINDOPRIL;(intermediate of perindopril);Indoles;Chiral Compound;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;Proline-Based Organocatalysts;Pharmaceutical Intermediates;Heterocycle-Indole series
• Mol File: 79815-20-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 177 °C (dec.)(lit.)
• Boiling Point: 290.25°C (rough estimate)
• Flash Point: 183.6 °C
• Appearance: Beige to brown/Powder
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 1.88E-06mmHg at 25°C
• Refractive Index: -116 ° (C=1, 2mol/L HCl)
• Storage Temp.: Store at 0°C
• PKA: 2.04±0.20(Predicted)
• Water Solubility: Slightly soluble in water
• CAS DataBase Reference: (S)-(-)-Indoline-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Indoline-2-carboxylic acid(79815-20-6)
• EPA Substance Registry System: (S)-(-)-Indoline-2-carboxylic acid(79815-20-6)

Safety Data

• Hazard Codes: Xn
• Statements: 43-48/22-62
• Safety Statements: 22-25-26-36/37
• WGK Germany: 2
• Hazardous Substances Data: 79815-20-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Catalyst for enantioselective cyclopropanations.

InChI:InChI=1/C9H9NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-4,8,10H,5H2,(H,11,12)/t8-/m1/s1

Synthetic route

l-(S)-2,3-dihydro-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-1H-indole-2-carboxylic acid (78779-29-0) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	100%

(S)-2-amino-3-(2-bromophenyl)propanoic acid (42538-40-9) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With potassium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 80 - 100℃; for 3.5 - 4h; Product distribution / selectivity;	95.9%
With potassium carbonate In water at 95℃; for 22h; Product distribution / selectivity;	95.6%
With potassium carbonate; copper(l) chloride In water at 95℃; for 1h; Inert atmosphere; enantioselective reaction;	83%

(S)-indoline-2-carboxylic acid methyl ester (141410-06-2) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Stage #1: (S)-indoline-2-carboxylic acid methyl ester With sodium hydroxide; water at 20℃; Stage #2: With hydrogenchloride; water at 20℃; pH=5;	94.5%

Indole-2-carboxylic acid (1477-50-5) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With carbon disulfide; carbon dioxide; hydrogen iodide; hydrogen; potassium iodide In ethanol at 90℃; for 5h; Temperature; Solvent; Autoclave; Large scale;	87.5%

(S)-2,3-Dihydro-1H-indole-2-carboxylic acid tert-butyl ester; compound with formic acid → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 3h; Heating;	87%

(S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester (110592-39-7) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With sulfuric acid; water Reflux;	86.8%

(S)-o-bromophenylalanine hydrochloride → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With potassium carbonate; copper(I) bromide In water at 100 - 105℃; Inert atmosphere;	86.2%

(2S)-2-amino-3-(2-chlorophenyl)propanoic acid (103616-89-3) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With potassium carbonate; copper(l) chloride In water at 95℃; for 40h; Product distribution / selectivity;	76.6%
Stage #1: (2S)-2-amino-3-(2-chlorophenyl)propanoic acid With potassium carbonate; copper(l) chloride In water at 95℃; for 40h; Stage #2: With water at 25℃; pH=3.5; Product distribution / selectivity; Acidic conditions;	76.6%

(2S)-indoline-2-carboxylic acid (R)-α-methylbenzylamine salt (79854-38-9) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With hydrogenchloride In water for 2h; Product distribution / selectivity;	52.8%

1-acetyl-2,3-indoline-2-carboxylic acid (82950-72-9) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With hydrogenchloride

1-benzhydryl-2,3-dihydro-1H-indole-2-carboxylic acid tert-butyl ester (496790-47-7) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr 2: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme

2-(benzhydrylidene-amino)-3-(2-bromo-phenyl)-propionic acid tert-butyl ester (496790-43-3) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / nBu3SnH; AIBN / benzene / 5 h / 85 °C 2: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr 3: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme

1-Bromo-2-bromomethyl-benzene (3433-80-5) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: CsOH*H2O / cinchonine bromide derived chiral / 20 h 2: 69 percent / nBu3SnH; AIBN / benzene / 5 h / 85 °C 3: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr 4: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 89 percent / CsOH*H2O / cinchonidinium bromide derived chiral / 20 h 2: 69 percent / nBu3SnH; AIBN / benzene / 5 h / 85 °C 3: 77 percent / H2 / Pd/C / methanol / 48 h / 5171.62 Torr 4: 87 percent / aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme

N-acetyl-indoline-2-carboxylic acid methyl ester (110659-07-9) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 43 percent 2: aq. 2N HCl View Scheme

indolin-2-yl carboxylic acid (16851-56-2) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: 52 percent / Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C 3: 1.) 4-(dimethylamino)pyridine 5: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 6: 100 percent / 6 N HCl / 3 h / Heating View Scheme

(S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester (50501-07-0) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / KOH / dimethylsulfoxide; H2O / Ambient temperature 2: 52 percent / Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C 4: 1.) 4-(dimethylamino)pyridine 6: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 7: 100 percent / 6 N HCl / 3 h / Heating View Scheme
Multi-step reaction with 7 steps 1: 100 percent / Et3N / diethyl ether / 4 h / Ambient temperature 2: 95 percent / NaOH / methanol; H2O / 1 h / Ambient temperature 4: 1.) 4-(dimethylamino)pyridine 6: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 7: 100 percent / 6 N HCl / 3 h / Heating View Scheme

2,3-dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester (78701-23-2) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: 95 percent / NaOH / methanol; H2O / 1 h / Ambient temperature 3: 1.) 4-(dimethylamino)pyridine 5: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 6: 100 percent / 6 N HCl / 3 h / Heating View Scheme

2,3-Dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid (78701-24-3) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 5 steps 2: 1.) 4-(dimethylamino)pyridine 4: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 5: 100 percent / 6 N HCl / 3 h / Heating View Scheme

(-)-1-(2-methyl-1-oxo-2-propenyl)indoline-2-carboxylic acid (78701-38-9) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) 4-(dimethylamino)pyridine 3: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 4: 100 percent / 6 N HCl / 3 h / Heating View Scheme

(S)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid (78701-25-4, 78701-28-7, 78779-25-6, 78779-26-7, 78779-27-8, 78779-28-9, 106517-52-6) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 3 steps 2: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 3: 100 percent / 6 N HCl / 3 h / Heating View Scheme

Wy-44,088 (78779-25-6) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / 2-methoxyethylamine / 0.42 h / 0 - 20 °C 2: 100 percent / 6 N HCl / 3 h / Heating View Scheme

indoline-2-carboxylic acid (R)-α-methylbenzylamine salt → (S)-indoline-2-carboxylic acid (79815-20-6) + (R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid (98167-06-7)

Conditions	Yield
With hydrogenchloride In water for 2h;

(S)-indoline-2-carboxylic acid (1S)-10-camphorsulfonic acid salt (887769-80-4) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With sodium hydroxide In water at 0 - 5℃; pH=2.9;

(+)-α-Chloro-2-aminobenzenepropanoic acid, 2,6-dimethylpiperidine salt (104145-74-6, 106025-43-8, 106025-50-7) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
With phosphorus pentaoxide; sodium hydroxide

C9H9NO2*C17H17Cl2N (880872-40-2) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Stage #1: C9H9NO2*C17H17Cl2N With sodium hydroxide In water; ethyl acetate pH=> 10; Stage #2: With hydrogenchloride In water pH=4 - 5;

6-amino-(S)-indoline-2-carboxylic acid (1344514-62-0) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Stage #1: 6-amino-(S)-indoline-2-carboxylic acid With hydrogenchloride In water at 0℃; for 0.5h; Stage #2: With sodium nitrite In water for 1h; Stage #3: With ethanol In water at 55℃; for 3h;	7 g

4-nitro-3-phenyl-L-alanine (949-99-5) → (S)-indoline-2-carboxylic acid (79815-20-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid; uronium nitrate / 5 h / 0 - 60 °C 2.1: oxygen; potassium carbonate / water / 5 h / 120 °C / 3000.3 Torr / Autoclave 3.1: 5%-palladium/activated carbon; hydrogen / water / 4 h / 60 °C / 3750.38 Torr / Autoclave 4.1: hydrogenchloride / water / 0.5 h / 0 °C 4.2: 1 h 4.3: 3 h / 55 °C View Scheme

ethanol (64-17-5) + (S)-indoline-2-carboxylic acid (79815-20-6) → Ethyl (S)-indoline-2-carboxylate hydrochloride (79854-42-5)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 16h;	100%
With thionyl chloride In ethanol at 0 - 20℃; for 16h;	100%
With thionyl chloride at 0 - 20℃; for 16h;	100%
With thionyl chloride

methanol (67-56-1) + (S)-indoline-2-carboxylic acid (79815-20-6) → (S)-indoline-2-carboxylic acid methyl ester hydrochloride

Conditions	Yield
With thionyl chloride at 0 - 20℃;	100%
With thionyl chloride at -10 - 20℃;	99%
With thionyl chloride at 20℃; for 53h; Esterification;	99%

methanol (67-56-1) + (S)-indoline-2-carboxylic acid (79815-20-6) → (S)-indoline-2-carboxylic acid methyl ester (141410-06-2)

Conditions	Yield
With thionyl chloride at 40℃; for 3h;	99%
With sulfuric acid at 80℃; for 16h;	89.01%
With thionyl chloride at 0 - 70℃; for 16h; Cooling with ice;	82%

(S)-indoline-2-carboxylic acid (79815-20-6) + benzyl chloroformate (501-53-1) → (S)-1-(benzyloxycarbonyl)indoline-2-carboxylic acid (104261-79-2)

Conditions	Yield
With sodium hydroxide at 0℃; for 1h;	99%
With sodium hydrogencarbonate In water; toluene Ambient temperature;	96%
With sodium hydroxide at 5 - 20℃; for 5h;	93%

di-tert-butyl dicarbonate (24424-99-5) + (S)-indoline-2-carboxylic acid (79815-20-6) → (S)-N-tert-butoxycarbonylindoline-2-carboxylic acid (144069-67-0)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 12h;	98%
With sodium carbonate In tert-butyl alcohol at 20℃; for 12h;	96%
With sodium hydroxide In 1,4-dioxane at 0 - 20℃;	90%

(S)-indoline-2-carboxylic acid (79815-20-6) → (2S)-2,3-dihydro-1H-indole-2-ylmethanol (27640-33-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether Inert atmosphere;	96%
Stage #1: (S)-indoline-2-carboxylic acid With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran Reflux; Stage #2: With hydrogenchloride; methanol; water In tetrahydrofuran Reflux; Stage #3: With sodium hydroxide In water	87%
Stage #1: (S)-indoline-2-carboxylic acid With dimethylsulfide borane complex In tetrahydrofuran for 12h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol for 2h; Reflux; Stage #3: With sodium hydroxide In tetrahydrofuran; methanol; water	87%

ethanol (64-17-5) + (S)-indoline-2-carboxylic acid (79815-20-6) → (S)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (82923-81-7)

Conditions	Yield
With thionyl chloride	95%
With thionyl chloride at 0 - 20℃; for 16h;

(S)-indoline-2-carboxylic acid (79815-20-6) + methyl iodide (74-88-4) → (2S)-1-methylindoline-2-carboxylic methyl ester (502435-12-3)

Conditions	Yield
With potassium carbonate In acetone at 50℃; for 24h; Inert atmosphere;	95%
With potassium carbonate In DMF (N,N-dimethyl-formamide); acetone at 20℃;

(S)-indoline-2-carboxylic acid (79815-20-6) → (6a,7,13a,14)-tetrahydropyrazino[1,2-a:4,5-a']diindol-6,13-dione (50501-06-9)

Conditions	Yield
In N,N-dimethyl-formamide at 220℃; under 12901.3 Torr; for 0.416667h; Microwave irradiation;	94%

(S)-indoline-2-carboxylic acid (79815-20-6) → (6aS-cis)-6a,7,13a,14-tetrahydropyrazino<1,2-a:4,5-a'>diindole-6,13-dione (104321-36-0)

Conditions	Yield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;	93%
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation;	93%
With triethylamine In toluene for 5h; Heating;	83%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 1h; Ambient temperature;	76%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 1h; Ambient temperature;	76%

(S)-indoline-2-carboxylic acid (79815-20-6) + chloro-diphenylphosphine (1079-66-9) → C33H27NO2P2

Conditions	Yield
With triethylamine In diethyl ether for 24h;	93%

sarcosine (107-97-1) + (S)-indoline-2-carboxylic acid (79815-20-6) → (S)-2-methyl-2,3,10,10a-tetrahydropyrazino[1,2-a]indole-1,4-dione (1110659-50-1)

Conditions	Yield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;	93%

di-tert-butyl dicarbonate (24424-99-5) + (S)-indoline-2-carboxylic acid (79815-20-6) → methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate (197460-36-9)

Conditions	Yield
Stage #1: (S)-indoline-2-carboxylic acid With thionyl chloride In methanol Inert atmosphere; Stage #2: di-tert-butyl dicarbonate With triethylamine Inert atmosphere;	91%
With thionyl chloride; triethylamine 1.) MeOH, -10 deg C, 0.5 h; reflux, 3 h, 2.) CH2Cl2, room temperature, 24 h; Yield given. Multistep reaction;

trifluorormethanesulfonic acid (1493-13-6) + (S)-indoline-2-carboxylic acid (79815-20-6) + 3-phenyl-propenal (104-55-2) → CF3O3S(1-)*C18H16NO2(1+)

Conditions	Yield
Stage #1: (S)-indoline-2-carboxylic acid; 3-phenyl-propenal In methanol at 20℃; for 0.0333333h; Stage #2: trifluorormethanesulfonic acid In methanol	91%

(S)-indoline-2-carboxylic acid (79815-20-6) + (R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid (98167-06-7) → indolin-2-yl carboxylic acid (16851-56-2)

Conditions	Yield
Stage #1: (S)-indoline-2-carboxylic acid; (R)-(-)-2,3-Dihydro-1H-Indole-2-Carboxylic Acid With sodium hydroxide In water at 170℃; under 5250.53 Torr; for 3h; Racemisation; Stage #2: With hydrogenchloride In water at 20 - 25℃; pH=3.4;	90%

(S)-indoline-2-carboxylic acid (79815-20-6) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
rhodium In 1,4-dioxane; methanol; water	86.1%
With 8 % Pd/C; hydrogen In methanol at 55 - 65℃; under 37503.8 Torr; Autoclave;	73.5%
With hydrogen; palladium on activated charcoal In acetic acid at 50℃; under 36775.4 Torr; for 18h;	66%

(S)-indoline-2-carboxylic acid (79815-20-6) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) + (2S,3aR,7aR)-octahydroindole-2-carboxylic acid (145513-90-2)

Conditions	Yield
With hydrogen; acetic acid; platinum(IV) oxide at 60℃; for 24h; atmospheric pressure;	A 85% B n/a
With platinum(IV) oxide; hydrogen at 60℃; optical yield given as %de;	A 85% B n/a

acetic anhydride (108-24-7) + (S)-indoline-2-carboxylic acid (79815-20-6) → 1-acetyl-2,3-indoline-2-carboxylic acid (82950-72-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	85%

(S)-indoline-2-carboxylic acid (79815-20-6) + L-proline (147-85-3) → (5aS,12aS)-1,2,3,5a,6,12a-hexahydro-5H,12H-pyrrolo[1',2':4,5]pyrazino[1,2-a]indole-5,12-dione (104261-77-0)

Conditions	Yield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;	83%

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) + (S)-indoline-2-carboxylic acid (79815-20-6) → (4aS,6aS,13aS,14aS)-1,2,3,4,4a,6a,7,13a,14,14a-decahydro-6H,13H-pyrazino[1,2-a:4,5-a']diindole-6,13-dione (1110659-49-8)

Conditions	Yield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;	81%

L-N-Boc-Ala (15761-38-3) + (S)-indoline-2-carboxylic acid (79815-20-6) → methyl (2S)-1-{(2S)-2-[(tert-butyloxycarbonyl)-amino]-propionyl}-2,3-dihydro-1H-indole-2-carboxylate

Conditions	Yield
Stage #1: (S)-indoline-2-carboxylic acid With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: L-N-Boc-Ala With dicyclohexyl-carbodiimide at 20℃; for 6h;	81%

(S)-indoline-2-carboxylic acid (79815-20-6) → Cbz-D-HPro-Ohi-OH + Ethyl (S)-indoline-2-carboxylate hydrochloride (79854-42-5)

Conditions	Yield
With hydrogenchloride In ethanol	A n/a B 78%
With hydrogenchloride In ethanol	A n/a B 78%
With hydrogenchloride In ethanol	A n/a B 78%
With hydrogenchloride In ethanol	A n/a B 78%
With hydrogenchloride In ethanol	A n/a B 78%

Upstream product

• 1477-50-5 Indole-2-carboxylic acid 
• 82950-72-9 1-acetyl-2,3-indoline-2-carboxylic acid 
• 50501-07-0 (S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester 
• 110592-39-7 (S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester 
• 89-98-5 2-chloro-benzaldehyde 
• 108906-13-4 (R,S)-indoline-2-carboxylic acid amide 
• 63-91-2 L-phenylalanine 
• 49607-21-8 (2S)-2-amino-3-(2,4-dinitrophenyl)propanoic acid 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 1344514-62-0 6-amino-(S)-indoline-2-carboxylic acid 
• 880872-40-2 C₉H₉NO₂*C₁₇H₁₇Cl₂N 
• 104145-74-6 (+)-α-Chloro-2-aminobenzenepropanoic acid, 2,6-dimethylpiperidine salt 
• 887769-80-4 (S)-indoline-2-carboxylic acid (1S)-10-camphorsulfonic acid salt 
• 79854-38-9 (2S)-indoline-2-carboxylic acid (R)-α-methylbenzylamine salt 

Downstream Products

• 82923-76-0 (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 82950-72-9 1-acetyl-2,3-indoline-2-carboxylic acid 
• 82834-16-0 Perindopril 
• 107133-36-8 perindopril tert-butylamine 
• 1239587-35-9 (2S)-1-[5-methoxy-2-nitro-4-(phenylmethoxy)-benzoyl]-2-indolinecarboxylic acid methyl ester 
• 1239587-36-0 (2S)-1-[5-methoxy-2-nitro-4-(phenylmethoxy)-benzoyl]-2-indolinealdehyde 
• 1239587-37-1 (S)-9-(benzyloxy)-8-methoxy-12a,13-dihydro-6H-benzo[5,6][1,4]diazepino[1,2-a]indol-6-one 
• 329015-60-3 N-cyclohexyl-(S)-N^α-(tert-butoxycarbonyl)indoline-2-carboxamide 
• 329015-66-9 N-(4-nitrophenyl)-(S)-N^α-(tert-butoxycarbonyl)indoline-2-carboxamide 
• 329015-63-6 N-(4-methoxyphenyl)-(S)-N^α-(tert-butoxycarbonyl)indoline-2-carboxamide 
• 329015-61-4 N-(o-tolyl)-(S)-N^α-(tert-butoxycarbonyl)indoline-2-carboxamide 
• 329015-59-0 N-phenyl-(S)-N^α-(tert-butoxycarbonyl)indoline-2-carboxamide 
• 305827-39-8 (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 

Relevant articles and documents

Semi-rational protein engineering of a novel esterase from Bacillus aryabhattai (BaCE) for resolution of (R,S)-ethyl indoline-2-carboxylate to prepare (S)-indoline-2-carboxylic acid

A gene encoding an esterase from Bacillus aryabhattai (BaCE) was identified, synthesized and efficiently expressed in the Escherichia coli system. A semi-rational protein engineering was applied to further improve the enzyme's enantioselectivity. Under the guidance of the molecular docking result, a single mutant BaCE-L86Q and a double mutant BaCE-L86Q/G284E were obtained, with its Emax value 6.4 times and 13.9 times of the wild-type BaCE, respectively. The recombinant BaCEs were purified and characterized. The overwhelming E value demonstrated that BaCE-L86Q/G284E was a promising biocatalyst for the biological resolution to prepare (S)-indoline-2-carboxylic acid.

Of enantiomerically enriched indoline - 2 - formic acid

The invention discloses a synthesis method of enantiomer-enriched indoline-2-formic acid shown in a formula (I). The synthesis method of the enantiomer-enriched indoline-2-formic acid comprises the following steps: by adopting low-cost and available ortho-position halogen substituted benzaldehyde and N-benzoyl substituted glycine as starting materials, carrying out Erlenmeyer-Plochl cyclization, alkaline hydrolysis and asymmetric catalytic hydrogen for constructing a chiral center, and then carrying out acid catalysis, deprotection and cyclization sequentially or cyclization, acid catalysis and deprotection sequentially, so that the enantiomer-enriched indoline-2-formic acid is obtained. The synthesis method of the enantiomer-enriched indoline-2-formic acid has the advantages that raw materials used in the whole process route are low-cost and easily available, harmful substances or multiple danger special processes are not used, reaction conditions are mild, technological operation is simple, production is safe and stable, the product yield is high, the purity is high, less three wastes are produced, and the energy consumption is low, so that the synthesis method of the enantiomer-enriched indoline-2-formic acid is a process route especially applicable to industrial production. The formula (1) is described in the specification.

Asymmetric synthesis of chiral heterocyclic amino acids via the alkylation of the Ni(II) complex of glycine and alkyl halides

An investigation into the reactivity profile of alkyl halides has led to the development of a new method for the asymmetric synthesis of chiral heterocyclic amino acids. This protocol involves the asymmetric alkylation of the Ni(II) complex of glycine to form an intermediate, which then decomposes to form a series of valuable chiral amino acids in high yields and with excellent diastereoselectivity. The chiral amino acids underwent a smooth intramolecular cyclization process to afford the valuable chiral heterocyclic amino acids in high yields and enantioselectivities. This result paves the way for the development of a new synthetic method for chiral heterocyclic amino acids.