Benzyl octahydro-1h-indole-2-carboxylate

Base Information

• Chemical Name: Benzyl octahydro-1h-indole-2-carboxylate
• CAS No.: 82717-90-6
• Molecular Formula: C16H21NO2
• Molecular Weight: 259.348
• DSSTox Substance ID: DTXSID30524986
• Mol file: 82717-90-6.mol

Synonyms:82717-90-6;benzyl octahydro-1h-indole-2-carboxylate;SCHEMBL2178522;DTXSID30524986;ARGCRCXTJMQKNA-UHFFFAOYSA-N;benzyl-perhydroindole-2-carboxylate;AKOS010531609;benzyloctahydro-1h-indole-2-carboxylate;EN300-122399;(2S, 3aR,7aS)-Benzyl octahydro -2-carboxylate-1H-indole

Chemical Property of Benzyl octahydro-1h-indole-2-carboxylate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 259.157228913
• Heavy Atom Count: 19
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)CC(N2)C(=O)OCC3=CC=CC=C3

Technology Process of Benzyl octahydro-1h-indole-2-carboxylate

There total 10 articles about Benzyl octahydro-1h-indole-2-carboxylate 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: 88.0%

octahydro-indole-2-carboxylic acid benzyl ester → cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester (82717-90-6)

Guidance literature:

In isopropyl alcohol; at 20 ℃; for 0.5h; Solvent;

Reference yield:

octahydroindole-2-carboxylic acid benzyl ester hydrochloride (82717-97-3) → cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester (82717-90-6)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 25 - 35 ℃; pH=9 - 11;

Reference yield:

(2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylic acid hydrochloride (1004292-98-1) + (2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylic acid tosylate + benzyl alcohol (100-51-6,185532-71-2) → benzyl (2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylate (82717-90-6,83508-14-9,107081-15-2,124002-35-3,144540-71-6)

Guidance literature:

(2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylic acid hydrochloride; (2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylic acid tosylate; benzyl alcohol; With toluene-4-sulfonic acid; In toluene; at 110 ℃; for 2.25h;

With sodium carbonate; In dichloromethane; water;

upstream raw materials:

(2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylic acid hydrochloride

benzyl alcohol

octahydroindole-2-carboxylic acid benzyl ester hydrochloride

cyclohexyl-N-tosyl aziridine

Downstream raw materials:

trandolapril benzyl ester

benzyl-2S,3aR,7aS-octahydroindole carboxylate camphor sulfonate

N-[1-(S)-carbethoxy-3-phenylpropyl]-(S)-alanyl-2R,3aS,7aR-octahydroindole-2-carboxylic acid

trandolapril

Refernces

• 1、 -. "PREPARATION OF TRANDOLAPRIL". Page/Page column 4; 8. . Retrieved 2010/11/28.
• 2、 -. "ANTIHYPERTENSIVE AGENTS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESSES FOR THE PREPARATION OF THE AGENTS AND COMPOSITIONS". . . Retrieved 2008/06/13.