83508-14-9

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-2-carboxylic acid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)is used as a potential therapeutic agent for neurological disorders, specifically Alzheimer's disease, due to its acetylcholinesterase inhibitory activity. This activity helps in enhancing cognitive function and slowing down the progression of the disease.
Used in Drug Synthesis:
1H-Indole-2-carboxylic acid, octahydro-, phenylmethyl ester, (2S,3aS,7aS)is used as a key intermediate in the synthesis of other important pharmaceutical compounds. Its unique chemical structure and properties make it a valuable building block for the development of novel drugs with potential therapeutic applications.

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 academic research and scientific papers

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.

A METHOD FOR THE PREPARATION OF (2S, 3AR, 7AS)-OCTAHYDRO-1H-INDOLE-2-CARBOXYLIC ACID AS KEY INTERMEDIATE IN THE PREPARATION OF TRANDOLAPRIL BY REACTING A CYCLOHEXYL AZIRIDINE WITH A DIALKYL MALONATE

A method for the synthesis of a compound of formula (I) as a mixture of enantiomers, formula (I) (wherein R1 is H or an acid protective group and H+A- indicates an optional acid with which the compound of formula (I) may form an ammonium salt) said method comprising; A) reacting a cyclohexyl aziridine with a dialkyl malonate, whereby to provide a trans-fused 3-alkylcarbonyl-octahydro-indol-2-one; B) decarbonylation at the 3-position, conversion of the ketone of the resulting trans-octahydro-indol-2-one to an optionally protected carboxylic acid group; and C) optionally removing any N-substitution if necessary.

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.