56269-65-9

Upstream product

• 107-13-1 acrylonitrile 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 166327-69-1 acetic acid 2-cyano-1-isopropyl-allyl ester 
• 350801-68-2 3-cyano-5-methyl-hex-3-enoic acid ethyl ester 

Relevant academic research and scientific papers

Method for synthesizing pregabalin from isobutyraldehyde

The present invention discloses a method for synthesizing pregabalin from isobutyraldehyde. The method comprises the following steps: performing Baylis-Hillman reaction on isobutyraldehyde and acrylonitrile by using DABCO and 2,6-di-tert-butylphenol as catalysts; performing substitution with 1-ethyl chloroformate in a solvent composed of pyridine and dichloroethane; performing carbonylation reaction on CO and ethanol by using palladium acetate and triphenylphosphine as catalysts; performing catalytic hydrogenation on raney nickel; performing hydrolysis in potassium hydroxide and methanol solvent, and adding acid for acid precipitation; and finally performing chiral resolution by using (S)-mandelic acid as a resolving agent. According to the method disclosed by the present invention, the inexpensive and easily available isobutyraldehyde is used as a raw material, and the pregabalin is obtained through Baylis-Hillman reaction, substitution reaction, carbonylation reaction, hydrogenation reaction, hydrolysis and acid precipitation and chiral resolution. The reaction route is simple, and the yield of the whole reaction is relatively high, so that overall yield and purity of the final pregabalin are ensured.

Versatile O- and S-functionalized 1,2,3-triazoliums: Ionic liquids for the Baylis-Hillman reaction and ligand precursors for stable MIC-transition metal complexes

The efficient synthesis of O- and S-functionalized 1,2,3-triazoliums is reported. Owing to their physical properties, these cations are efficient ionic liquids for Baylis-Hillman addition under mild reaction conditions. Simultaneously, the functionalizati

Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure

Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.

Highly efficient synthesis of novel Morita-Baylis-Hillman adducts from activated ketones using a DABCO-based hydroxy ionic liquid (HIL) as a recyclable catalyst-solvent

A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita-Baylis-Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita-Baylis-Hill

Asymmetric organocatalysed [1,3]-sigmatropic rearrangements

The first organocatalysed enantioselective [1,3]-sigmatropic O- to N-rearrangement reactions are presented. The reactions take place under regio- and enantioselective control, and are catalysed by cinchona alkaloids. Two reactions have been developed the first one is the rearrangement of imidates to amides, while the other rear rangement occurs from carbamates to amines via a decarboxylation. Both transformations give nitrogen protected β-amino acid derivatives as the product. These novel asymmetric organocatalysed [1,3]-sigmatropic O- to N-rearrangement reactions provide a reliable and efficient synthetic method for obtaining enantioenriched β-amino acid derivates in good yield from racemic starting materials.

Asymmetric synthesis of pregabalin

This invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid (pregabalin) or a salt thereof via an asymmetric hydrogenation synthesis. Pregabalin is useful for the treatment and prevention of seizure disorders, pain, and psychotic disorders. The invention also provides intermediates useful in the production of pregabalin.

Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope

The reactivity of a variety of quinuclidine-based catalysts in the Baylis-Hillman reaction has been examined, and a straightforward correlation between the basicity of the base and reactivity has been established, without exception. The following order of

An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation

A concise enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid (1, Pregabalin) has been developed. The key step is the asymmetric hydrogenation of a 3-cyano-5-methylhex-3-enoic acid salt 2 with a rhodium Me-DuPHOS catalyst, providing the desired (S)-3-cyano-5-methylhexanoate 3 in very high ee. Subsequent hydrogenation of the nitrile 3 with a heterogeneous nickel catalyst provides Pregabalin I in excellent overall yield and purity.

Nucleophile-Catalysed Additions of Aldehydes and Ketones to Acrylic Compounds: The Effectiveness of High Pressures

The preparation of a wide range of compounds of general type: CH2=C(Z)-CR1R2OH (Z = CN, COOR, CHO,; R1,R2 = H, alkyl, aryl) from the reaction of CH2=CHZ with aldehydes and ketones, is effectively catalysed by tertiary amines especially DABCO.Rates are found to be very strongly accelerated by high pressures (2-10 kbar) which alone permits the additions of ketones or of crotonic acid derivatives to take place.In the absence of carbonyl acceptors novel oligomers of acrylic compounds form.

A Simple Synthesis of 2-(1-Hydroxyalkyl)acrylonitriles

2-(1-Hydroxyalkyl)acrylonitriles are conveniently prepared in excellent yields by the reaction of acrylonitile with a variety of aldehydes catalyzed by 1,4-diazabicyclooctane (DABCO).