155666-94-7

Basic information

• Product Name: N-trifluoroacetyl-(R)-1-aminoindan
• Synonyms: N-trifluoroacetyl-(R)-1-aminoindan
• CAS NO: 155666-94-7
• Molecular Weight: 229.202
• Mol File: 155666-94-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: N-trifluoroacetyl-(R)-1-aminoindan(CAS DataBase Reference)
• NIST Chemistry Reference: N-trifluoroacetyl-(R)-1-aminoindan(155666-94-7)
• EPA Substance Registry System: N-trifluoroacetyl-(R)-1-aminoindan(155666-94-7)

Safety Data

• Hazardous Substances Data: 155666-94-7(Hazardous Substances Data)

Usage

Description

N-trifluoroacetyl-(R)-1-aminoindan is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique molecular structure, which includes a trifluoroacetyl group and an (R)-1-aminoindan moiety. N-trifluoroacetyl-(R)-1-aminoindan plays a significant role in the development of medications targeting specific biological pathways.

Uses

Used in Pharmaceutical Industry:
N-trifluoroacetyl-(R)-1-aminoindan is used as an intermediate in the synthesis of (3R)-2,3-Dihydro-3-(2-propyn-1-ylamino)-1H-inden-1-one (D449765). N-trifluoroacetyl-(R)-1-aminoindan is a vital building block in the preparation of Rasagiline (R126000), a selective irreversible MAO-B inhibitor. Rasagiline is employed as an Antiparkinsonian agent, helping to alleviate the symptoms of Parkinson's disease by targeting the monoamine oxidase B enzyme, which is involved in the breakdown of dopamine in the brain.

Upstream product

• 10277-74-4 (R)-1-Aminoindane 
• 83-33-0 inden-1-one 
• 407-25-0 trifluoroacetic anhydride 
• 169105-02-6 N-[(1R)-2,3-dihydro-1H-inden-1-yl]acetamide 
• 10305-73-4 (R)-2,3-dihydro-1H-inden-1-amine hydrochloride 

Downstream Products

• 161735-79-1 rasagiline mesylate 
• 136236-51-6 rasagiline 
• 209394-27-4 ladostigil 
• 947674-87-5 N-[(R)-6-hydroxyindan-1-yl]carbamic acid tert-butyl ester 
• 169105-01-5 (R)-3-amino-2,3-dihydro-1H-inden-5-ol 

Relevant articles and documents

Asymmetric Full Saturation of Vinylarenes with Cooperative Homogeneous and Heterogeneous Rhodium Catalysis

Homogeneous and heterogeneous catalyzed reactions can seldom operate synergistically under the same conditions. Here we communicate the use of a single rhodium precursor that acts in both the homogeneous and heterogeneous phases for the asymmetric full saturation of vinylarenes that, to date, constitute an unmet bottleneck in the field. A simple asymmetric hydrogenation of a styrenic olefin, enabled by a ligand accelerated effect, accounted for the facial selectivity in the consecutive arene hydrogenation. Tuning the ratio between the phosphine ligand and the rhodium precursor controlled the formation of homogeneous and heterogeneous catalytic species that operate without interference from each other. The system is flexible in terms of both the chiral ligand and the nature of the external olefin. We anticipate that our findings will promote the development of asymmetric arene hydrogenations.

COMPOUNDS WITH NEURAL PROTECTIVE EFFECT, AND PREPARATION AND USE THEREOF

The invention generally relates to compounds of formula (I) with neural protective effect, and preparation and uses thereof. The compounds have multiple mechanisms or functions, for example, inhibition of monoamine oxidase and cholinesterase, scavenging of free radicals, and protection of cells such as nerve cells. The compounds can be used for manufacture of medicaments of cell protection, for prevention and/or treatment of monoamine oxidase, cholinesterase and free radicals related diseases, for example, neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease and stroke, and free-radical related diseases such as heart disease, myocardial ischemia, diabetes and other cardiovascular and cerebrovascular diseases.

NEW METHOD FOR THE SYNTHESIS OF RASAGILINE

We have developed a new method for the synthesis of Rasagiline (Formula 1) based on the alkylation of trifluoroacetyl protected aminoindan. This protection enabled us to carry out an alkylation of aminoindan with a high yield and purity under very mild conditions with a wide range of reaction conditions and reagent selection. Considering the ease, purity and high yields of introducing and removal of the trifluoroacetyl group, this approach is a highly practical and economical way for the synthesis of rasagiline or its pharmaceutically acceptable salts.