83508-14-9

Basic information

• Product Name: 1H-Indole-2-carboxylicacid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)-
• Synonyms: 1H-Indole-2-carboxylicacid, octahydro-, phenylmethyl ester, [2S-(2a,3ab,7ab)]-; (2S,3aS,7aS)-Octahydro-1H-indole-2-carboxylic acidbenzyl ester; Benzyl (2S,3aS,7aS)-perhydroindole-2-carboxylate
• CAS NO: 83508-14-9
• Molecular Formula: C16H21 N O2
• Molecular Weight: 259.348
• Mol File: 83508-14-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Indole-2-carboxylicacid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylicacid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)-(83508-14-9)
• EPA Substance Registry System: 1H-Indole-2-carboxylicacid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)-(83508-14-9)

Safety Data

• Hazardous Substances Data: 83508-14-9(Hazardous Substances Data)

Usage

General Description

1H-Indole-2-carboxylic acid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)- is a chemical compound that belongs to the class of carboxylic acid esters. It is commonly known as (-)-Eseroline, and is a natural product found in the seeds of the tropical plant species Psychotria longipes. (-)-Eseroline has been studied for its potential pharmacological properties, particularly its activity as an acetylcholinesterase inhibitor. This enzyme inhibition activity makes it a potential candidate for the treatment of neurological disorders such as Alzheimer's disease. Additionally, (-)-Eseroline has been investigated for its potential use in the synthesis of other important pharmaceutical compounds.

Upstream product

• 80875-98-5 (2S,3aS,7aS)-perhydroindole-2-carboxylic acid 
• 100-51-6 benzyl alcohol 
• 1004292-98-1 (2SR,3aRS,7aSR)-octahydro-1H-indole-2-carboxylic acid hydrochloride 

Downstream Products

• 122454-52-8 (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid benzyl ester 
• 98677-37-3 trandolapril benzyl ester 
• 80875-98-5 (2S,3aS,7aS)-perhydroindole-2-carboxylic acid 
• 82834-16-0 Perindopril 
• 149-30-4 2-Mercaptobenzothiazole 

Relevant articles and documents

Process for the preparation of intermediates of perindopril

A process for the preparation of (2S, 3aS, 7aS)perhydroindole-2-carboxylic acid is provided comprising (a) esterifying a cis-perhydroindole-2-carboxylic acid with a first alcohol of the formula ROH and a suitable free acid to provide the acid salt (AS) of Formula V: (b) reacting the acid salt of Formula V with a first base to provide a compound of Formula VI: (c) treating the product of step (b) with an L-tartaric containing acid in a second alcohol of the formula ROH to precipitate a compound of Formula VII: (d) reacting the compound of Formula VII with a second base to provide a compound of Formula II (e) hydrolyzing the compound of Formula II to provide the (2S, 3aS, 7aS)perhydroindole-2-carboxylic acid.

Asymmetric Synthesis of Proline Derivatives from (2R) and (2S)-2-tert-Butyl-3-Benzoyl-4-Methyleneoxazolidin-5-one

The conjugate addition of enamines (2a,b) to the chiral oxazolidinones (1) or ent-(1) favours cis 2,4-substituted oxazolidinone adducts while trans 2,4-substituted oxazolidinone adducts are favoured from the addition reactions of enamine (2c).The diastereomeric adducts from the addition of (2a) to (1) are readily separated and can be converted to (5R,2S) and (5S,2R) 5-iso-propyl proline efficiently and in good overall yield.The extenstion of this protocol to the synthesis of perhydroindole carboxylic acid suffered from poor overall stereochemical control.