30683-77-3

Upstream product

• 110164-82-4 3-bromo-3a,4,5,6,7,7a-hexahydrobenzo[d]isoxazole 
• 286-20-4 cyclohexane-1,2-epoxide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 143-33-9 sodium cyanide 
• 4513-77-3 2-cyanocyclohexanone 
• 646-20-8 pimelonitrile 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 70367-40-7 3a,4,5,6,7,7a-hexahydro-3-methoxy-1,2-benzisoxazole 

Downstream Products

• 153541-15-2 (1S,2S)-1-cyano-2-(trimethylsilyloxy)cyclohexane 
• 265096-49-9 (1S,2R)-trans-2-hydroxy-1-cyanocyclohexane trimethylsilyl ether 
• 182698-20-0 (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether 
• 1044502-74-0 cis-bis(2-hydroxycyclohexanecarbonitrile)dichloroplatinum (II) 

Relevant academic research and scientific papers

Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles

A stereoselective bioreduction of 2-oxocycloalkanecarbonitriles was concurrently coupled to a whole cell-catalyzed nitrile hydrolysis in one-pot. The first step, mediated by ketoreductases, involved a dynamic reductive kinetic resolution, which led to 2-hydroxycycloalkanenitriles in very high enantio- and diastereomeric ratios. Then, the simultaneous exposure to nitrile hydratase and amidase from whole cells of Rhodococcus rhodochrous provided the corresponding 2-hydroxycycloalkanecarboxylic acids with excellent overall yield and optical purity for the all-enzymatic cascade.

Highly regioselective conversion of epoxides to β-hydroxy nitriles using metal(II) Schiff base complexes as new catalysts under mild conditions

Epoxides undergo efficient ring opening with potassium cyanide in acetonitrile in the presence of metal Schiff base complexes as catalysts. This method was carried out under neutral and mild conditions with both high yields and high regioselectivity within a short period of time. Thus, several β-hydroxy nitriles, useful intermediates for the synthesis of biologically active molecules, were easily obtained at room temperature.

Metal(II) Schiff base complexes as catalysts for the high-regioselective conversion of epoxides to β-hydroxy nitriles in glycol solvents

A facile preparation of 3-hydroxy propanenitrile derivatives is described involving ring opening of epoxides with potassium cyanide in glycol solvents in the presence of Schiff base complexes as catalysts. This method occurs under neutral and mild conditions with high yields and high regioselectivity. Thus, several β-Hydroxy nitriles, useful intermediates toward biologically-active molecules, are easily obtained at room temperature.

Ring opening of 3-bromo-2-isoxazolines to β-hydroxy nitriles

3-Bromo-2-isoxazolines were converted to the corresponding β-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave β-hydroxy nitriles under relatively mild conditio

Preparation of β-hydroxyesters from isoxazolines. A selective Ni 0bpy-catalyzed electrochemical method

An electrocatalytic method for the reductive N-O cleavage of isoxazolines is described. Ni0bpy, generated in situ, was used to promote selective ring opening of 3-methoxy-5-phenylisoxazoline (1a) and 3-methoxy-[4,5]cyclohexylisoxazoline (1b). DMF and NaI were used as solvent and supporting electrolyte, and β-hydroxyesters 2a and 2b were obtained in high yields respectively, after acid hydrolysis. β-Hydroxynitriles 3a and 3b were also identified as side products.

Dynamic kinetic resolution of 2-oxocycloalkanecarbonitriles: Chemoenzymatic syntheses of optically active cyclic β- and γ-amino alcohols

A series of fungi and yeasts have been tested for the stereoselective bioreduction of 2-oxocycloalkanecar-bonitriles, 1. The yeast Saccharomyces montanus CBS 6772 yielded the corresponding cis-hydroxy nitriles, 2, in >90% ee and de and in high chemical yields. Through simple and efficient procedures, they were transformed into optically active 2-amino and 2-aminomethyl cycloalkanols.

Ring opening of epoxides with sodium cyanide catalyzed with Ce(OTf)4

Efficient and regioselective conversion of epoxides to β-hydroxy nitriles with sodium cyanide in the presence of catalytic amounts of Ce(OTf)4 is described under solvent free conditions.

Practical oxirane ring opening with in situ prepared LiCN; synthesis of (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1 -butanenitrile

Trisubstituted oxirane 1 was regiospecifically opened with LiCN in situ prepared from acetone cyanohydrin and LiH to provide the corresponding β-hydroxy nitrile 2 in satisfactory yield, enabling us to manufacture a key intermediate for a new antifungal agent on a multi-kg scale. Some applications of this method to the ring opening of other oxiranes and nucleophilic substitution are also described.

A new method for the preparation of β-hydroxy nitriles; Transformation of 3-bromo-2-isoxazolines to β-hydroxy nitriles by treatment of alkanethiolates

3-Bromo-2-isoxazolines are transformed to β-hydroxy nitriles in good yields by treatment with alkanethiolates under a very mild condition.