Production Method 1

79815-20-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

(Mercaptopropanoyl)indoline-2-carboxylic acids and related compounds as potent angiotensin converting enzyme inhibitors and antihypertensive agents

Kim, Dong H.; et al, Journal of Medicinal Chemistry, 1983, 26(3), 394-403

Production Method 2

42538-40-9

79815-20-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cuprous chloride Solvents: Water ;  rt → 95 °C; 22 h, 95 °C; 95 °C → 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3.5 - 7.6

Reference

Asymmetric Synthesis of (S)-2-Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis

de Lange, Ben; et al, ChemCatChem, 2011, 3(2), 289-292

Production Method 3

3770-50-1

79815-20-6

Reaction Conditions

1.1 -
2.1 -
3.1 Catalysts: 1-Phenylethylamine

Reference

Industrial preparation of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid as intermediate for antihypertensive perindopril

, European Patent Organization, , ,

Production Method 4

1477-50-5

79815-20-6

Reaction Conditions

1.1 -
2.1 -
3.1 -
4.1 Catalysts: 1-Phenylethylamine

Reference

Industrial preparation of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid as intermediate for antihypertensive perindopril

, European Patent Organization, , ,

Production Method 5

116586-57-3

79815-20-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  3 h, reflux
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Free Radical-Mediated Aryl Amination and Its Use in a Convergent [3 + 2] Strategy for Enantioselective Indoline α-Amino Acid Synthesis

Viswanathan, Rajesh; et al, Journal of the American Chemical Society, 2003, 125(1), 163-168

Production Method 6

1222073-43-9

79815-20-6

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Water ;  4 h, 0.5 MPa, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0.5 h, 0 °C
1.3 Reagents: Sodium nitrite ;  0 °C; 1 h, 0 °C
1.4 Solvents: Ethanol ;  3 h, 55 °C

Reference

Transformation of L-phenylalanine to (S)-indoline-2-carboxylic acid without group-protection

Liu, Jin-Qiang; et al, Research on Chemical Intermediates, 2013, 39(3), 1143-1152

Production Method 7

104758-16-9

79815-20-6

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Enzymic resolution of indoline-2-carboxylic acid esters

, European Patent Organization, , ,

Production Method 8

103616-89-3

79815-20-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cuprous chloride Solvents: Water ;  rt → 95 °C; 2 h, 95 °C; 95 °C → 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3.5 - 7.6

Reference

Asymmetric Synthesis of (S)-2-Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis

de Lange, Ben; et al, ChemCatChem, 2011, 3(2), 289-292

Production Method 9

50501-07-0

79815-20-6

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Enzymic resolution of indoline-2-carboxylic acid esters

, European Patent Organization, , ,

Production Method 10

50501-07-0

79815-20-6

Reaction Conditions

1.1 -
2.1 Catalysts: 1-Phenylethylamine

Reference

Industrial preparation of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid as intermediate for antihypertensive perindopril

, European Patent Organization, , ,

Production Method 11

104758-15-8

79815-20-6

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Enzymic resolution of indoline-2-carboxylic acid esters

, European Patent Organization, , ,

Production Method 12

79815-20-6

Reaction Conditions

1.1 Catalysts: Triacylglycerol lipase

Reference

Enzymic resolution of indoline-2-carboxylic acid esters

, European Patent Organization, , ,

(2S)-2,3-dihydro-1H-indole-2-carboxylic acid Raw materials

• H-Phe(2-Cl)-OH
• Ethyl Indoline-2-carboxylate
• 1H-Indole-2-carboxylic acid, 2,3-dihydro-6-nitro-, (2S)-
• 1H-Indole-2-carboxylic acid, 2,3-dihydro-, pentyl ester
• 1H-Indole-2-carboxylic acid, 2,3-dihydro-, 1,1-dimethylethyl ester, (2S)-
• L-2-Bromophenylalanine
• Ethyl indole-2-carboxylate
• 1H-Indole-2-carboxylic acid, 2,3-dihydro-, butyl ester
• Indole-2-carboxylic acid

(2S)-2,3-dihydro-1H-indole-2-carboxylic acid Preparation Products

• (2S)-2,3-dihydro-1H-indole-2-carboxylic acid (79815-20-6)

• 1. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 2. Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties?
  S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. Lee RSC Adv., 2014,4, 23107-23115
• 3. An approach to the structure and vibrational analysis of cis- and trans-3-chlorostyrene through IR/Raman and INS spectroscopies and theoretical ab initio/DFT calculations?
  J. M. Granadino-Roldán,M. Fernández-Gómez,A. Navarro,T. Pe?a Ruiz,U. A. Jayasooriya Phys. Chem. Chem. Phys., 2004,6, 1133-1143
• 4. Achieving crystal-induced room temperature phosphorescence and reversible photochromic properties by strong intermolecular interactions?
  Fuming Xiao,Mengzhu Wang,Yunxiang Lei,Wenbo Dai,Yunbing Zhou,Miaochang Liu,Wenxia Gao,Xiaobo Huang,Huayue Wu J. Mater. Chem. C, 2020,8, 17410-17416
• 5. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
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• Catalysts and Inorganic Chemicals Catalysts

Chemical Profile of (2S)-2,3-dihydro-1H-indole-2-carboxylic Acid (CAS No. 79815-20-6)

(2S)-2,3-dihydro-1H-indole-2-carboxylic acid, identified by its CAS number 79815-20-6, is a significant compound in the field of pharmaceutical chemistry and bioorganic synthesis. This molecule, belonging to the indole derivatives family, has garnered attention due to its versatile structural framework and potential biological activities. The stereochemistry at the 2-position, specifically the (S) configuration, plays a crucial role in determining its pharmacological properties and interactions with biological targets.

The indole core is a privileged scaffold in medicinal chemistry, widely recognized for its presence in numerous bioactive natural products and pharmacologically relevant molecules. The carboxylic acid functionality at the 2-position of the indole ring introduces reactivity that allows for further derivatization, making this compound a valuable intermediate in the synthesis of more complex molecules. The addition of the dihydropyran ring system at the 3-position further enhances its structural complexity and potential for modulating biological responses.

Recent advancements in computational chemistry and molecular modeling have highlighted the importance of stereochemistry in drug design. The (S)-configuration of (2S)-2,3-dihydro-1H-indole-2-carboxylic acid has been shown to influence its binding affinity and selectivity when interacting with enzymes and receptors. Studies have demonstrated that subtle changes in stereochemistry can lead to significant differences in pharmacological activity, emphasizing the need for precise structural control during drug development.

In the realm of drug discovery, (2S)-2,3-dihydro-1H-indole-2-carboxylic acid has been explored as a precursor for various therapeutic agents. Its indole moiety is closely associated with molecules that exhibit antimicrobial, anti-inflammatory, and anticancer properties. For instance, derivatives of this compound have shown promise in inhibiting specific enzymatic pathways implicated in cancer progression. The carboxylic acid group also facilitates conjugation with other functional groups, enabling the design of prodrugs or targeted delivery systems.

The synthesis of (2S)-2,3-dihydro-1H-indole-2-carboxylic acid involves multi-step organic transformations that highlight the ingenuity of synthetic chemists. One common approach involves the reduction of an indolecarboxaldehyde derivative followed by stereoselective functionalization at the 2-position. Advances in asymmetric catalysis have enabled more efficient and scalable methods for producing enantiomerically pure forms of this compound, which is critical for pharmaceutical applications where stereochemical purity is paramount.

Recent research has also explored the role of (2S)-2,3-dihydro-1H-indole-2-carboxylic acid in modulating neurotransmitter systems. Indole derivatives are known to interact with serotonin receptors, which are implicated in mood regulation and neurological disorders. The carboxylic acid group provides a handle for further modifications that could enhance binding affinity or selectivity for specific serotonin receptor subtypes. This has opened up avenues for developing novel therapeutics targeting conditions such as depression and anxiety.

The compound's structural features make it an attractive candidate for further exploration in medicinal chemistry. Its ability to undergo diverse chemical transformations while maintaining biological relevance underscores its utility as a building block for drug discovery programs. As computational methods continue to evolve, virtual screening techniques are being employed to identify new derivatives with enhanced pharmacological profiles.

Industrial applications of (2S)-2,3-dihydro-1H-indole-2-carboxylic acid are also emerging beyond academic research. Pharmaceutical companies are increasingly leveraging this compound as a key intermediate in large-scale syntheses of active pharmaceutical ingredients (APIs). The availability of high-quality starting materials like this one streamlines the drug development process, reducing costs and timelines associated with producing complex molecules.

The future direction of research on (2S)-2,3-dihydro-1H-indole-2-carboxylic acid is likely to focus on expanding its therapeutic applications and optimizing synthetic routes for scalability. Collaborative efforts between synthetic chemists and biologists will be essential in unlocking the full potential of this versatile compound. As our understanding of biological systems grows more sophisticated, so too will our ability to design molecules that precisely target disease mechanisms.

In conclusion, (2S)-2,3-dihydro-1H-indole-2-carboxylic acid (CAS No. 79815-20-6) represents a compelling example of how structural diversity can drive innovation in drug discovery. Its unique combination of functional groups and stereochemical features makes it a valuable asset in both academic research and industrial applications. Continued exploration into its biological activities and synthetic possibilities promises to yield novel therapeutic agents that address unmet medical needs.

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