293737-30-1

Basic information

• Product Name: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2R)-(9CI)
• Synonyms: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2R)-(9CI);(R)-2,3-dihydro-1H-indol-2-carboxylic acid Methyl ester
• CAS NO: 293737-30-1
• Molecular Formula: C10H11NO2
• Molecular Weight: 0
• Product Categories: PYRROLE
• Mol File: 293737-30-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2R)-(9CI)(293737-30-1)
• EPA Substance Registry System: 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2R)-(9CI)(293737-30-1)

Safety Data

• Hazardous Substances Data: 293737-30-1(Hazardous Substances Data)

Usage

Also known as

(R)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester

Structure

Bicyclic aromatic heterocycle

Derivative of

Indole

Usage

Intermediate in the synthesis of various pharmaceuticals and organic compounds

Importance

Building block in organic synthesis with applications in the pharmaceutical and chemical industries

Stereoisomeric configuration

(2R)-(9CI)

Upstream product

• 109-21-7 butyl butyrate 
• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 1210801-46-9 N-(2-(bromomethyl)phenyl)-4-methyl-benzenesulfonamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 71-36-3 butan-1-ol 
• 721968-93-0 3-methoxyphenyl allyl carbonate 
• 15022-08-9 diallylcarbonate 

Relevant articles and documents

Production of optically active aromatic compounds having nitrogen atoms in a ring structure comprising

PROBLEM TO BE SOLVED: To provide a production method for obtaining an optically active aromatic compound having a cyclic structure including a nitrogen atom, in which a modified group can be removed while keeping a high yield and optical purity, with a high yield in a high enantioselective manner.SOLUTION: An aromatic compound described below is used as a substrate: in the aromatic compound, an amino group expressed by -NHR11 (where R11 is an arene sulfonyl group) is bonded to one of two carbon atoms constituting a benzene ring and adjoining to each other, and -R13-CHR15-C(=O)-Z (where R13 represents a methylene or an ethylene which may have a substituent, R15 represents a hydrogen atom, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent, and Z represents a heteroaryl group which may have a substituent) is bonded to the other carbon atom. The substrate is made to react in a system to which N-spiro C2 axis asymmetric quaternary ammonium iodide and an oxidizing agent are supplied so as to obtain an aromatic compound having a cyclic structure including a nitrogen atom derived from the above amino group.

Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution

A series of α-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate.