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Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S,4S,8R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-8-vinyl-1-azoniabicyclo[2.2.2]octane bromide is used as a precursor in the synthesis of pharmaceutical compounds due to its unique structure and potential biological activity. The presence of the quinoline moiety, which is known for its diverse pharmacological properties, makes it a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (1S,2S,4S,8R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-8-vinyl-1-azoniabicyclo[2.2.2]octane bromide serves as a versatile building block for the creation of various organic compounds. Its unique structure, including the bromide ion and the vinyl group, allows for further functionalization and modification, enabling the synthesis of a wide range of organic molecules with different properties and applications.
Used in Material Science:
(1S,2S,4S,8R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-8-vinyl-1-azoniabicyclo[2.2.2]octane bromide can be utilized in material science for the development of novel materials with specific properties. (1S,2S,4S,8R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-8-vinyl-1-azoniabicyclo[2.2.2]octane bromide's chiral centers and functional groups may contribute to the creation of materials with unique optical, electronic, or mechanical characteristics, making it suitable for applications in various industries, such as electronics, nanotechnology, and polymer science.

Upstream product

• 32247-96-4 3,5-bis(trifluoromethyl)benzyl bromide 
• 130-95-0 Quinine 
• 56-54-2 quinindine 
• 130-95-0 quinine 
• 56-54-2 quinidine 

Relevant academic research and scientific papers

Development and Scale-up of an Organocatalytic Enantioselective Process to Manufacture (S)-Pregabalin

Herein is reported the development of a new process to manufacture (S)-pregabalin. The method comprises six steps, run under the catalysis of a recyclable polymer bound phase transfer catalyst, and afforded (S)-pregabalin in overall 54% yield, starting from building blocks acetylacetone, isovaleraldehyde, and nitromethane.

Asymmetric Synthesis of α-Amino Phosphonates by Using Cinchona Alkaloid-Based Chiral Phase Transfer Catalyst

A highly enantioselective nucleophilic addition of phosphite esters to imines catalyzed by a chiral phase-transfer catalyst has been developed. The process affords the hydrophosphonylation of imine products with quaternary stereocenters in good to high yields (up to 95 % yield) and excellent enantioselectivities (up to 99 % ee).

Asymmetric synthesis of β-amino ketones by using cinchona alkaloid-based chiral phase transfer catalysts

A highly enantioselective nucleophilic addition of ketones to imines catalyzed by chiral phase-transfer catalysts (N-quaternised cinchona alkaloid ammonium salts) has been developed, and the process affords the Mannich reaction products with tertiary stereocenters in good to high yields (up to 95%) with excellent enantioselectivities (up to 97% ee).

Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: An effective route to dezocine

In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7- methoxy-2-tetralone with 1, 5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective.

DIHYDROISOXAZOLE COMPOUND FOR USE IN CONTROLLING SEA LICE

The present invention provides a dihydroisoxazole of formula: or a salt thereof, for use in the control of sea lice in fish.

Catalytic asymmetric conjugate addition of isocyanoacetate to (Z)-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor

(Z)-3-Substituted-2-(4-pyridyl)-acrylonitriles, a reactive class of Michael acceptors obtained exclusively as a single (Z) isomer, reacted with un-substituted isocyanoacetate esters mediated by phase-transfer catalysis to give, after base promoted cyclisation, functionalized imines in up to 94% ee and as a single diastereoisomer.

The enantioselective trifluoromethylation of aromatic aldehydes by quaternary ammonium bromide and (IPr)CuF at low catalyst loading

A general catalytic enantioselective trifluoromethylation of aromatic aldehydes using (IPr)CuF and quinidine-derived quaternary ammonium salt as catalysts has been developed. A wide range of aromatic aldehydes are converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading.

Diastereoselective and enantioselective epoxidation of acyclic β-trifluoromethyl-β,β-disubstituted enones by hydrogen peroxide with a pentafluorinated quinidine-derived phase-transfer catalyst

An efficient catalytic asymmetric epoxidation of β-trifluoromethyl- β,β-disubstituted unsaturated ketones has been achieved by a pentafluorine-substituted phase-transfer catalyst with hydrogen peroxide (30%). Thus, the β-trifluoromethyl-α,β-epoxy ketones with a quaternary carbon centre were obtained in excellent diastereoselectivities (up to 100:1 dr) and excellent enantioselectivities (up to 99.7% ee). Low catalyst loading, recycle of catalyst, environmentally benign oxidant and easy transformation of the epoxides into medicinally important trifluoromethylated intermediate make our protocol much more practical. Copyright

PROCESS FOR THE PREPARATION OF GAMMA AMINO ACIDS AND INTERMEDIATES USED IN SAID PROCESS

The invention relates to the preparation of gamma amino acids of formula (I) and pharmaceutically acceptable salts, solvates and prodrugs thereof, and to intermediates used for their preparation. (formula I) wherein R1 is selected from an alkyl group, an alkenyl group, an alkynyl group and a cycloalkyl group, each of which may be optionally substituted and * denotes a chiral centre. In particular, the present invention provides an efficient synthesis of (S)-pregabalin which is suitable for carrying out on an industrial scale.

Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt

A general enantioselective trifluoromethylation of aldehydes has been developed using (IPr)CuF and quinidine-derived quaternary ammonium salt as the cooperative catalyst. Thus, a wide range of aromatic aldehydes have been converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. The greatly enhanced activity and enantioselectivity result from the initiative generation of active [(IPr)CuCF3] as well as additional coordination activation of other copper species.