1231763-32-8

Basic information

• Product Name: 9-Amino-(9-deoxy)epi-quinine trihydrochloride
• Synonyms: (8α,9S)-6′-Methoxycinchonan-9-amine trihydrochloride ;(8alpha,9S)-6'-Methoxycinchonan-9-amine trihydrochloride >=90%;(S)-{5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl}-(6-methoxyquinolin-4-yl)methanamine trihydrochlo;(8α, 9S)-6'-Methoxycinchonan-9-amine trihydrochloride, min. 90%;(S)-(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanamine:trihydrochloride;9S)-6'-Methoxycinchonan-9-amine trihydrochloride, min. 90%
• CAS NO: 1231763-32-8
• Molecular Formula: C20H28Cl3N3O
• Molecular Weight: 432.81482
• Mol File: 1231763-32-8.mol
• Article Data: 6

Chemical Properties

• Appearance: pale yellow/Powder
• Stability: store cold
• CAS DataBase Reference: 9-Amino-(9-deoxy)epi-quinine trihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Amino-(9-deoxy)epi-quinine trihydrochloride(1231763-32-8)
• EPA Substance Registry System: 9-Amino-(9-deoxy)epi-quinine trihydrochloride(1231763-32-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 1231763-32-8(Hazardous Substances Data)

Usage

Reaction

Aza-Michael reactions on α,β-unsaturated ketones. Epoxidation of α,β-unsaturated ketones. Epoxidation of α,β-unsaturated aldehydes. Nitrocyclopropanation of α,β-unsaturated ketones. Diels-Alder reaction. Intramolecular aldolization of diketones. Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones. Friedel-Crafts/amination cascade reactions with a-substituted α,β-unsaturated aldehydes. Aziridination of acyclic α,β-unsaturated ketones. Aziridination of cyclic α,β-unsaturated ketones. Double Michael cascade process. α-fluorination of cyclic ketones.

Chemical Properties

Solid

Upstream product

• 130-95-0 Quinine 
• 168778-61-8 (8S,9S)-9-azido-(9-deoxy)epiquinine 
• 130-95-0 quinine 
• 168778-61-8 (8S,9S)-9-azido-(9-deoxy)epiquinine 
• 130-95-0 quinine 
• 56-54-2 qunidine 

Downstream Products

• 1630973-03-3 C₃₉H₃₈N₃O₂P 
• 1630973-06-6 2-(diphenylphosphino)-N-((S)-((1S,2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl)benzamide 
• 852913-53-2 9-amino-9-deoxy-epihydroquinine 

Relevant articles and documents

Enantioselective Alkylative Kinetic Resolution of 2-Oxindole-Derived Enolates Promoted by Bifunctional Phase Transfer Catalysts

The first strategy for bringing about highly enantioselective alkylative enolate kinetic resolutions using a simple phase-transfer protocol via SN2 chemistry has been developed. In the presence of a new squaramide-based quaternized cinchona alkaloid-derived catalyst and aqueous base, benzyl, allyl, and propargyl halides react with racemic substituted oxindoles to generate densely functionalized products with the two contiguous stereocenters, one of which is an all-carbon quaternary.

Dynamic kinetic resolution of bis-aryl succinic anhydrides: Enantioselective synthesis of densely functionalised γ-butyrolactones

The efficient Dynamic Kinetic Resolution (DKR) of disubstituted anhydrides has been shown to be possible for the first time. Using an ad hoc designed organocatalyst and an enantio- and diastereoselective cycloaddition process with aldehydes, stereochemically complex γ-butyrolactone derivatives can be obtained-with control over three contiguous stereocentres, one of which is all carbon quaternary.

Cinchona alkaloid derivatives, their process of preparation and their use as catalysts

The present invention provides a process for preparing a substantially stereochemically pure compound of formula (I), or a salt thereof wherein R1 and R2 are independently selected from the group consisting of H, -CH2-CH3, and -CH=CH2, the process comprising the step of demethylating the corresponding methylated compound of formula (II) in the presence of an alkaline or alkaline earth metal (C1-C10) alkylthiolate salt and a polar aprotic solvent.