87679-20-7

Basic information

• Product Name: 1H-Indole-2-carboxylicacid,octahydro-,(2-alpha-,3a-alpha-,7a-alpha-)-(9CI)
• Synonyms: 1H-Indole-2-carboxylicacid,octahydro-,(2-alpha-,3a-alpha-,7a-alpha-)-(9CI)
• CAS NO: 87679-20-7
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.2209
• Product Categories: PYRROLE
• Mol File: 87679-20-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-2-carboxylicacid,octahydro-,(2-alpha-,3a-alpha-,7a-alpha-)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylicacid,octahydro-,(2-alpha-,3a-alpha-,7a-alpha-)-(9CI)(87679-20-7)
• EPA Substance Registry System: 1H-Indole-2-carboxylicacid,octahydro-,(2-alpha-,3a-alpha-,7a-alpha-)-(9CI)(87679-20-7)

Safety Data

• Hazardous Substances Data: 87679-20-7(Hazardous Substances Data)

Usage

Chemical Class

Indole carboxylic acids

Bicyclic Structure

Octahydroindole core with a carboxylic acid functional group

Stereochemistry

2-alpha-, 3a-alpha-, 7a-alpha-

Also known as

cis-perhydroindole-2-carboxylic acid

Usage

Building block in the synthesis of pharmaceuticals and other organic compounds

Potential Applications

Pharmaceutical industry due to structural features and biological activities

Other Applications

Industrial and research applications in organic synthesis and chemical reactions

Upstream product

• 59224-99-6 trans-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 1193-68-6 cis-octahydroindole 
• 89226-35-7 N-[(1S,2R)-2-(2-Chloro-2-cyano-ethyl)-cyclohexyl]-acetamide 
• 87623-93-6 (3aR,7aR)-1-(Octahydro-indol-1-yl)-ethanone 
• 4169-27-1 cis-3,4,4a,5,6,7,8,8a-Octahydro-2(1H)-quinolinone 
• 120-72-9 indole 
• 3770-50-1 2-carbethoxyindole 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 79799-08-9 (2S,3aS,7aS)-Octahydro-indole-2-carboxylic acid ethyl ester 
• 87623-95-8 (2R,3aS,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 87623-95-8 (2S,3aR,7aR)-1-Acetyl-octahydro-indole-2-carbonitrile 
• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 87624-03-1 (4aR,8aS)-3-Chloro-octahydro-quinolin-2-one 

Downstream Products

• 80876-00-2 (2α,3aβ,7aβ)-octahydro-1H-indole-2-carboxylic acid 1,1-dimethylethyl ester 
• 82717-91-7 (+/-)-benzyl (2S,3aS,7aS)-octahydroindole-2-carboxylate p-toluenesulfonic acid salt 
• 1609090-02-9 C₂₀H₂₈NO₉P 
• 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 
• 1555994-24-5 (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol 
• 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 
• 852921-57-4 N-[1-(S)-carbethoxy-3-phenylpropyl]-(S)-alanyl-2R,3aS,7aR-octahydroindole-2-carboxylic acid 
• 87679-37-6 trandolapril 
• 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 

Relevant articles and documents

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.