145513-93-5

Basic information

• Product Name: 1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aR)-(9CI)
• Synonyms: 1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aR)-(9CI);Perindopril Related Compound 5
• CAS NO: 145513-93-5
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.22
• Product Categories: PYRROLE
• Mol File: 145513-93-5.mol

Chemical Properties

• Boiling Point: 318.6±25.0 °C(Predicted)
• Appearance: /
• Density: 1.135±0.06 g/cm3(Predicted)
• PKA: 2.47±0.20(Predicted)
• CAS DataBase Reference: 1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aR)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aR)-(9CI)(145513-93-5)
• EPA Substance Registry System: 1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aR)-(9CI)(145513-93-5)

Safety Data

• Hazardous Substances Data: 145513-93-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-2-carboxylic acid, octahydro-, (2S,3aS,7aR)-(9CI) is used as a reactant for the preparation of stereoisomers of perindopril and perindoprilate. These stereoisomers are important components in the development of antihypertensive drugs, which help in the treatment of high blood pressure and other cardiovascular conditions. The specific stereochemistry of 1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aR)-(9CI) allows for the selective synthesis of the desired pharmaceutical products, ensuring their efficacy and safety in medical applications.

Upstream product

• 87624-03-1 (4aR,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 4169-27-1 cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 1193-68-6 cis-octahydroindole 
• 87623-93-6 (3aR,7aR)-1-(Octahydro-indol-1-yl)-ethanone 
• 120-72-9 indole 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 87623-95-8 (2S,3aR,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 3770-50-1 2-carbethoxyindole 
• 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 
• 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

• 80828-12-2 (2R,3aR,7aR)-1-(3-Acetylsulfanyl-propionyl)-octahydro-indole-2-carboxylic acid 
• 82717-91-7 (+/-)-benzyl (2S,3aS,7aS)-octahydroindole-2-carboxylate p-toluenesulfonic acid salt 
• 1555994-20-1 (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-22-3 (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-24-5 (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol 
• 1555994-26-7 (2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-29-0 (2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1555994-31-4 (2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 
• 1609090-02-9 C₂₀H₂₈NO₉P 
• 80828-33-7 tert-butyl (2S,3aS,7aS)-1-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)octahydro-1H-indole-2-carboxylate 
• 80828-33-7 (2S,3aS,7aS)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester 
• 80876-04-6 (2R,3aR,7aR)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester 
• 80828-33-7 (2R,3aR,7aR)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid tert-butyl ester 
• 108449-50-9 (2S,3aS,7aS)-1-[(S)-2-((R)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-indole-2-carboxylic acid 

Relevant articles and documents

The synthesis of trans-perhydroindolic acids and their application in asymmetric domino reactions of aldehyde esters with β,γ-unsaturated α-keto esters

(2S,3aR,7aS)-Perhydroindolic acid, the key intermediate in the synthesis of trandolapril, and its trans-isomers, were readily prepared. These proline-like molecules are unique in that they contain a rigid bicyclic structure, with two hydrogen atoms trans to each other at the bridgehead carbon atoms. These molecules were used successfully as chiral organocatalysts in asymmetric domino Michael addition/cyclization reactions of aldehyde esters with β,γ-unsaturated α-keto esters. They proved to have excellent catalytic behavior, allowing for the synthesis of multi-substituted, enantiomerically enriched hemiacetal esters. Under optimal conditions (using 10 mol% catalyst loading), a series of β,γ-unsaturated α-keto esters was examined with up to 99% de, ee and yield, respectively. Additionally, the enantiomerically enriched hemiacetal esters could be readily transformed into their corresponding bioactive pyrano[2,3-b]pyrans (possessing a multi-substituted bicyclic backbone). Copyright

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.

DIASTEREOSELECTIVE SYNTHESIS OF BICYCLIC AMINO ACIDS VIA RING CONTRACTION OF α-CHLOROLACTAMS

Bicyclic lactams were converted to their α-chloro-derivatives and subjected to ring contraction under basic conditions to give bicyclic acids in diasteroselective fashion.

COUPLING OF β-ACETAMIDO RADICALS WITH α-CHLORO ACRYLONITRILE - A NEW ACCESS TO DISUBSTITUTED PROLINE DERIVATIVES

β-Acetamido radicals are prepared by reduction of organomercurials and coupled with α-chloro-acrylonitrile.The coupling products are further converted to proline derivatives.