80875-98-5

Basic information

• Product Name: L-Octahydroindole-2-carboxylic acid
• Synonyms: OCTAHYDRO-INDOLE-2-CARBOXYLIC ACID;(2S,3αS,7αS)-Octahydro-1H-indole-2-carboxylic acid;(2S,3aS,7aS)-Octahydro-2-indolecarboxylicacid;[2S-(2a,3ab,7ab)]-Octahydro-1H-indole-2-carboxylic Acid;L-(2S,3aS,7aS)-Octahydroindole-2-carboxylic Acid;(2s,3as,7as)-Octahydro-1h-Indo;1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aS)-(9CI);(2S,3aS,7aS)-2-Carboxyperhydroindole
• CAS NO: 80875-98-5
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.22
• EINECS: 1592732-453-0
• Product Categories: PYRROLE;Indoles and derivatives;PERINDOPRIL;(intermediate of perindopril);Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Perindopril-Tert-Butylamine;Heterocycle-Indole series
• Mol File: 80875-98-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 275-277°C
• Boiling Point: 318.6 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: White solid
• Density: 1.135 g/cm³
• Vapor Pressure: 7.54E-05mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Store at 0°C
• Solubility: Methanol (Sparingly), Water (Slightly)
• PKA: 2.47±0.20(Predicted)
• Water Solubility: Soluble in methanol and water.
• CAS DataBase Reference: L-Octahydroindole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-Octahydroindole-2-carboxylic acid(80875-98-5)
• EPA Substance Registry System: L-Octahydroindole-2-carboxylic acid(80875-98-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37
• Hazardous Substances Data: 80875-98-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 80875-98-5 differently. You can refer to the following data:
1. An intermediate in the synthesis of Perindopril. Perindopril USP Related Compound A.
2. An intermediate in the synthesis of Perindopril

InChI:InChI=1/C9H15NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h6-8,10H,1-5H2,(H,11,12)/t6-,7-,8-/m0/s1

Synthetic route

(2S,3aS,7aS)-1-Benzoyl-octahydro-indole-2-carboxylic acid (80875-99-6) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
With hydrogenchloride In water for 4h; Heating;	87.8%

Benzyl (2S)-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylate (539820-41-2) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
With hydrogen; acetic acid; platinum on carbon at 20℃; under 3750.38 Torr;	87%

(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

ethyl (2S,3aS,7aS)-octahydro-1H-indole-2-carboxylate hydrochloride (82864-25-3) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;

(2S,3aS,7aS)-1-Acetyl-octahydro-indole-2-carboxylic acid tert-butyl ester (116795-46-1) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
With hydrogenchloride

rac-3-bromocyclohexene (1521-51-3) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Multi-step reaction with 7 steps 1: 89 percent / K2CO3 / acetonitrile / 48 h / Ambient temperature 2: 97 percent / K2CO3 / acetone / 48 h / Ambient temperature 3: 90 percent / 2N NaOH / dimethylformamide / 48 h / Ambient temperature 5: tetrahydrofuran / 0.5 h / Ambient temperature; Irradiation 6: Raney nickel 7: 6N HCl View Scheme

Ethyl (S)-indoline-2-carboxylate hydrochloride (79854-42-5) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / Pd/C / ethanol 2: NaOH / H2O; ethanol / 25 °C View Scheme

benzyl (S)-(S)-(S)-perhydroindole-2-carboxylate (83508-14-9) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Stage #1: benzyl (S)-(S)-(S)-perhydroindole-2-carboxylate With methanol; sodium hydroxide; water for 2h; Heating / reflux; Stage #2: With hydrogenchloride; water In methanol pH=6 - 7;

ethyl (2α, 3aβ, 7aβ)-octahydro-1H-indole-2-carboxylate (89083-53-4) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Stage #1: ethyl (2α, 3aβ, 7aβ)-octahydro-1H-indole-2-carboxylate With sodium hydroxide; water at 30 - 35℃; for 5h; Stage #2: With hydrogenchloride In water pH=4.5 - 4.8;

2-chloro-benzaldehyde (89-98-5) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: sodium acetate; acetic anhydride / 0.5 h / 20 °C / Inert atmosphere 1.2: 90 - 100 °C 2.1: sodium / 40 - 50 °C / Inert atmosphere 3.1: hydrogen; [Rhcod(S)-DuanPhos]BF4 / ethanol / 45 - 55 °C / 15001.5 Torr / Autoclave 4.1: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere 5.1: sulfuric acid; water / Reflux 6.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave View Scheme

(4Z)-4-[(2-chlorophenyl)methylene]-2-methyl-1,3-oxazol-5-one → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium / 40 - 50 °C / Inert atmosphere 2: hydrogen; [Rhcod(S)-DuanPhos]BF4 / ethanol / 45 - 55 °C / 15001.5 Torr / Autoclave 3: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere 4: sulfuric acid; water / Reflux 5: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave View Scheme

(Z)-2-acetylamino-3-(2-chlorophenyl)acrylic acid methyl ester → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen; [Rhcod(S)-DuanPhos]BF4 / ethanol / 45 - 55 °C / 15001.5 Torr / Autoclave 2: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere 3: sulfuric acid; water / Reflux 4: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave View Scheme

methyl (S)-2-acetamido-3-(2-chlorophenyl)propionate → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere 2: sulfuric acid; water / Reflux 3: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave View Scheme

(S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester (110592-39-7) → (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; water / Reflux 2: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave View Scheme

di-tert-butyl dicarbonate (24424-99-5) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (2S,3aS,7aS)-1-(tert-butoxycarbonyl)octahydro-1H-indole-2-carboxylic acid (109523-13-9)

Conditions	Yield
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With sodium hydroxide In tetrahydrofuran; water for 0.166667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 20℃; for 12h;	100%
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With sodium hydroxide In 1,4-dioxane; water at 0℃; for 0.333333h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃; Inert atmosphere;	99%
With triethylamine In tetrahydrofuran; water at 20℃;	98%

(1R,2R)-trans-2-phenylcyclopropane-1-carboxyl chloride (37107-48-5) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (2S,3aS,7aS)-1-((1R,2R)-2-Phenyl-cyclopropanecarbonyl)-octahydro-indole-2-carboxylic acid (176797-40-3)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran Ambient temperature;	100%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid

Conditions	Yield
With sodium carbonate In water; acetone at 20℃; Cooling with ice;	99%
With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Cooling with ice; Inert atmosphere;	73%

methanol (67-56-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (2S,3aS,7aS)-methyl octahydro-1H-indole-2-carboxylate (192436-84-3)

Conditions	Yield
With thionyl chloride at 20℃; Inert atmosphere;	98%
With thionyl chloride at 20℃; Cooling with ice;	93%
With thionyl chloride at 20℃;
With thionyl chloride

methanol (67-56-1) + chloroformic acid ethyl ester (541-41-3) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (2S,3aS,7aS)-1-ethyl 2-methyl hexahydro-1H-indole-1,2(2H,3H)-dicarboxylate (1213770-22-9)

Conditions	Yield
With potassium carbonate at 20℃; for 48h; Inert atmosphere;	98%
With potassium carbonate at 20℃; for 48h; Inert atmosphere;	98%
With potassium carbonate at 20℃; for 48h; Inert atmosphere;	96%

acetic anhydride (108-24-7) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 1-acetyl-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid

Conditions	Yield
In dichloromethane for 0.5h;	98%
In dichloromethane for 2.25h;

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (4aS,6aS,7aS,11aS,13aS,14aS)-hexadecahydropyrazino[1,2-a:4,5-a']diindol-6,13-dione

Conditions	Yield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;	97%

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) + benzyl chloroformate (501-53-1) → (2S,3aS,7aS)-1-(benzyloxycarbonyl)octahydro-1H-indole-2-carboxylic acid (107045-53-4)

Conditions	Yield
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.0833333h; Stage #2: benzyl chloroformate In tetrahydrofuran; water at 0 - 20℃; for 2h; Stage #3: pH=3; Acidic conditions;	96%
With sodium hydrogencarbonate In water; toluene at 0 - 20℃;	95%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 4h;	95%

formaldehyd (50-00-0) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → C10H17NO2

Conditions	Yield
Stage #1: formaldehyd; (2S,3aS,7aS)-perhydroindole-2-carboxylic acid In water for 0.166667h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 3h;	96%

(E)-1-methyl-3-(2-nitrovinyl)-1H-indole (2731-00-2, 122631-39-4) + 6-bromoisatin (6326-79-0) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 6-bromo-2'-(1-methyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	96%

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (2S,3aS,7aS)-(octahydro-indol-2-yl)-methanol

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether	95%
Multi-step reaction with 2 steps 1: thionyl chloride / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether Inert atmosphere;

(E)-1-methyl-3-(2-nitrovinyl)-1H-indole (2731-00-2, 122631-39-4) + 5-fluoro-1H-indole-2,3-dione (443-69-6) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-fluoro-2'-(1-methyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	95%

3-[(E)-2-nitroeth-1-enyl]-1H-indole (3156-51-2, 51870-94-1) + indole-2,3-dione (91-56-5) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 2'-(1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	94%

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) + toluene-4-sulfonic acid (104-15-4) + benzyl alcohol (100-51-6) → (2S,3aS,7aS)-octahydro-1H-indole-2-carboxylic acid phenylmethyl ester 4-methylbenzenesulfonate (94062-52-9)

Conditions	Yield
In toluene for 4h; Heating;	93%
In toluene Heating / reflux;	91%

7-chloroisatin (7477-63-6) + 3-[(E)-2-nitroeth-1-enyl]-1H-indole (3156-51-2, 51870-94-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 7-chloro-2'-(1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	93%

3-[(E)-2-nitroeth-1-enyl]-1H-indole (3156-51-2, 51870-94-1) + 5-Bromo-1H-indole-2,3-dione (87-48-9) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-bromo-2'-(1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	93%

3-(β-nitro-β-methylvinyl)indole (64252-02-4) + 5-Bromo-1H-indole-2,3-dione (87-48-9) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-bromo-2'-(1-methyl-1H-indol-3-yl)-1'-methyl-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	93%

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → ramipril

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In DMF (N,N-dimethyl-formamide); acetonitrile at 20℃; for 0.5h;	92%

5-methyl-indole-2,3-dione (608-05-9) + (E)-1-methyl-3-(2-nitrovinyl)-1H-indole (2731-00-2, 122631-39-4) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-methyl-2'-(1-methyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	92%

5-fluoro-1H-indole-2,3-dione (443-69-6) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) + (E)-1-methyl-3-(2-nitroprop-1-en-1-yl)-1H-indole (110999-33-2) → 5-fluoro-1'-methyl-2'-(1-methyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	92%

5-chloroindole 2,3-dione (17630-76-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) + (E)-1-methyl-3-(2-nitroprop-1-en-1-yl)-1H-indole (110999-33-2) → 5-chloro-1'-methyl-2'-(1-methyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	92%

(E)-1-methyl-3-(2-nitrovinyl)-2-phenyl-1H-indole (122631-44-1) + 5-Bromo-1H-indole-2,3-dione (87-48-9) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-bromo-2'-(1-methyl-2-phenyl-1H-indol-3-yl)-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	92%

5-methoxyisatine (39755-95-8) + 3-[(E)-2-nitroeth-1-enyl]-1H-indole (3156-51-2, 51870-94-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 2'-(1H-indol-3-yl)-5-methoxy-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	92%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 3-[(E)-2-nitroeth-1-enyl]-1H-indole (3156-51-2, 51870-94-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-fluoro-2'-(1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	92%

sarcosine (107-97-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → (5aS,9aS,10aS)-2-methyldecahydropyrazino[1,2-a]indole-1,4-dione (1110659-51-2)

Conditions	Yield
With methyl dichlorophosphite; triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 145℃; for 1h; Microwave irradiation; stereoselective reaction;	91%

(E)-1-methyl-3-(2-nitrovinyl)-1H-indole (2731-00-2, 122631-39-4) + 5-methoxyisatine (39755-95-8) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-methoxy-2'-(1-methyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	91%

5-fluoro-1H-indole-2,3-dione (443-69-6) + (E)-1-methyl-3-(2-nitrovinyl)-2-phenyl-1H-indole (122631-44-1) + (2S,3aS,7aS)-perhydroindole-2-carboxylic acid (80875-98-5) → 5-fluoro-2'-(1-methyl-2-phenyl-1H-indol-3-yl)-1'-nitro-1',2',4a',5',6',7',8',8a',9',9a'-decahydrospiro[indoline-3,3'-pyrrolo[1,2-a]indol]-2-one

Conditions	Yield
In ethanol; water at 20℃; for 6h; Green chemistry;	91%

Upstream product

• 3770-50-1 2-carbethoxyindole 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 1193-68-6 cis-octahydroindole 
• 87623-93-6 (3aR,7aR)-1-(Octahydro-indol-1-yl)-ethanone 
• 4169-27-1 cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 120-72-9 indole 
• 87623-95-8 (2S,3aR,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 79799-08-9 (2S,3aS,7aS)-Octahydro-indole-2-carboxylic acid ethyl ester 
• 59224-99-6 trans-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 87624-03-1 (4aR,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 89226-35-7 N-[(1S,2R)-2-(2-Chloro-2-cyano-ethyl)-cyclohexyl]-acetamide 
• 87623-95-8 (2R,3aS,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 

Downstream Products

• 108395-26-2 (2S,3aS,7aS)-1-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-octahydro-indole-2-carboxylic acid 
• 80828-15-5 (2α,3aβ,7aβ)-1-<3-(acetylthio)-2-methyl-1-oxopropyl>octahydro-1H-indole-2-carboxylic acid 
• 80828-15-5 (2R,3aR,7aR)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-octahydro-indole-2-carboxylic acid 
• 80828-31-5 (2α,3aβ,7aβ)-1-benzoyloctahydro-1H-indole-2-carboxylic acid 
• 107045-53-4 (2S,3aS,7aS)-1-(benzyloxycarbonyl)octahydro-1H-indole-2-carboxylic acid 
• 80876-00-2 (2α,3aβ,7aβ)-octahydro-1H-indole-2-carboxylic acid 1,1-dimethylethyl ester 
• 80876-00-2 (2α,3aβ,7aβ)-octahydro-1H-indole-2-carboxylic acid tert-butyl ester 
• 82717-91-7 (+/-)-benzyl (2S,3aS,7aS)-octahydroindole-2-carboxylate p-toluenesulfonic acid salt 
• 960529-89-9 benzyl (2R,3aR,7aR)-N-(tert-butoxycarbonyl)octahydroindole-2-carboxylate 
• 960529-90-2 benzyl (2S,3aS,7aS)-N-(tert-butoxycarbonyl)octahydroindole-2-carboxylate 
• 109523-13-9 (2S,3aS,7aS)-1-(tert-butoxycarbonyl)octahydro-1H-indole-2-carboxylic acid 
• 80875-98-5 (2S,3aS,7aS)-perhydroindole-2-carboxylic acid 
• 80875-99-6 (2S,3aS,7aS)-1-Benzoyl-octahydro-indole-2-carboxylic acid 
• 108395-27-3 (6aα,10aα,11aα)-decahydro-1H,5H-<1,4>thiazepino<4,3-a>indole-1,5-dione 

Relevant articles and documents

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.

Versatile methodology for the synthesis and α-functionalization of (2R,3aS,7aS)-octahydroindole-2-carboxylic acid

An improved strategy for the effective synthesis of enantiomerically pure (2R,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic), based on the?formation of a trichloromethyloxazolidinone derivative, has been developed. Additionally, the completely diastereoselective α-alkylation of such oxazolidinone provides a very convenient and concise route to enantiopure α-tetrasubstituted derivatives of this Oic stereoisomer.

Efficient access to N-protected derivatives of (R,R,R)- and (S,S,S)-octahydroindole-2-carboxylic acid by HPLC resolution

The preparation of the proline analogue (2S,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic) and its enantiomer, (2R,3aR,7aR)-Oic, is described. A racemic precursor has been synthesized in good yield and subjected to HPLC resolution on a chiral column. The high efficiency of both the synthetic and chromatographic procedures has allowed the isolation of multigram quantities of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis.