(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid
• CAS No.: 145438-94-4
• Molecular Formula: C9H15NO2
• Molecular Weight: 169.224
• Hs Code.: 2933990090
• European Community (EC) Number: 604-474-5
• DSSTox Substance ID: DTXSID30427049
• Nikkaji Number: J532.161A
• Wikidata: Q27464679
• Mol file: 145438-94-4.mol

Synonyms:145438-94-4;(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid;(2S,3aR,7aS)-Octahydroindole-2-carboxylic acid;87679-58-1;(2S,3AR,7AS)-OCTAHYDRO-INDOLE-2-CARBOXYLIC ACID;(2S,3AR,7aS)-rel-octahydro-1H-indole-2-carboxylic acid;(2S,3ar,7as)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylic acid;(2S,3AR,7aS)-rel-octahydro-1H- indole-2-carboxylic acid;(2S,3aR,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indol-1-ium-2-carboxylate;L-Octahydroindole-2-carboxylic acid;L-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid;1H-Indole-2-carboxylic acid, octahydro-, (2S,3aR,7aS)-;SCHEMBL497280;rel-(2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid;DTXSID30427049;CQYBNXGHMBNGCG-CSMHCCOUSA-N;BCP16126;FD7165;MFCD09952530;AKOS006284740;AKOS015854020;AM84415;AC-28351;AS-49299;CS-0375707;(2S,3aR,7aS)-perhydroindole-2-carboxylic acid;A808370;(2S, 3aR,7aS)-Octahydro-indole-2-carboxylic acid;(2S,3aR,7aS) octahydro-1H-indole-2-carboxylic acid;(2S,3aR,7aS)-octahydro-1H-indol-2-carboxylic acid;Q27464679;(2S, 3aR,7aS)-rel-Octahydro-indole-2-carboxylic acid;(2S,3AR,7aS)-rel-octahydro-1H-indole-2-carboxylicacid;rel-(2S, 3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid;(3aalpha,7abeta)-Octahydro-1H-indole-2alpha-carboxylic acid

Chemical Property of (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 7.54E-05mmHg at 25°C
• Melting Point: 307-309 °C (dec.)
• Refractive Index: 1.507
• Boiling Point: 318.6 °C at 760 mmHg
• PKA: 2.47±0.20(Predicted)
• Flash Point: 146.5 °C
• PSA: 49.33000
• Density: 1.135 g/cm³
• LogP: 1.32050
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated, Sonicated), Methanol (Sparingly, Heated, Sonicated), Wat
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 169.110278721
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

(2S,3aR,7aS)-Octahydroindole-2-carboxylicAcid(~90%,containscis) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)CC(N2)C(=O)O
• Isomeric SMILES: C1CC[C@H]2[C@H](C1)C[C@H](N2)C(=O)O
• Uses: (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid acts as a Trandolapril intermediate. Trandolapril intermediate.

Technology Process of (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid

There total 20 articles about (2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(2S,3aR,7aS-octahydroindole)-2-carboxylic acid-benzyl ester (144540-71-6) → (2S,3aR,7aS)-octahydroindolecarboxylic acid (145438-94-4,2055118-14-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 48h; under 15001.5 Torr;

DOI:10.1002/adsc.201200456

Reference yield: 85.0%

(2R,3aS,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile (87623-95-8,88500-10-1,89226-37-9,89226-38-0) → rac-trans-octahydroindole-2-carboxylic acid (80828-13-3,80875-98-5,82717-40-6,87679-20-7,87679-39-8,87679-51-4,87679-58-1,88547-85-7,88585-94-8,96844-78-9,108507-42-2,145438-94-4,145438-95-5,145513-90-2,145513-91-3,145513-92-4,145513-93-5,2055118-14-2)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1016/S0040-4039(00)87864-8

Reference yield: 70.0%

indolin-2-yl carboxylic acid (16851-56-2,78348-24-0) → (+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid (80828-13-3,80875-98-5,82717-40-6,87679-20-7,87679-39-8,87679-51-4,87679-58-1,88547-85-7,88585-94-8,96844-78-9,108507-42-2,145438-94-4,145438-95-5,145513-90-2,145513-91-3,145513-92-4,145513-93-5,2055118-14-2) + (+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid (80828-13-3,80875-98-5,82717-40-6,87679-20-7,87679-39-8,87679-51-4,87679-58-1,88547-85-7,88585-94-8,96844-78-9,108507-42-2,145438-94-4,145438-95-5,145513-90-2,145513-91-3,145513-92-4,145513-93-5,2055118-14-2)

Guidance literature:

With hydrogen; acetic acid; platinum(IV) oxide; at 60 ℃; for 24h;

DOI:10.1016/j.tetasy.2007.09.006

upstream raw materials:

(4aR,8aS)-3-Chloro-octahydro-quinolin-2-one

(2R,3aS,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile

N-[(1S,2R)-2-(2-Chloro-2-cyano-ethyl)-cyclohexyl]-acetamide

trans-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone

Downstream raw materials:

(2α,3aβ,7aβ)-1-<3-(acetylthio)-2-methyl-1-oxopropyl>octahydro-1H-indole-2-carboxylic acid

(2R,3aR,7aR)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-octahydro-indole-2-carboxylic acid

(+/-)-benzyl (2S,3aS,7aS)-octahydroindole-2-carboxylate p-toluenesulfonic acid salt

trandolapril