The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Hydroxy-3-phenylpropanenitrile( cas:17190-29-3 ) is researched.Safety of 3-Hydroxy-3-phenylpropanenitrile.Kamal, Ahmed; Khanna, G. B. Ramesh; Ramu, R. published the article 《Chemoenzymatic synthesis of both enantiomers of fluoxetine, tomoxetine and nisoxetine: lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles》 about this compound( cas:17190-29-3 ) in Tetrahedron: Asymmetry. Keywords: aryl hydroxyphenylpropanenitrile preparation ring opening styrene oxide sodium cyanide; kinetic resolution aryl hydroxyphenylpropanenitrile transesterification lipase catalyst; chemoenzymic preparation enantiomer fluoxetine tomoxetine nisoxetine. Let’s learn more about this compound (cas:17190-29-3).
A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alc. and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C Amano’ II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.
In addition to the literature in the link below, there is a lot of literature about this compound(3-Hydroxy-3-phenylpropanenitrile)Safety of 3-Hydroxy-3-phenylpropanenitrile, illustrating the importance and wide applicability of this compound(17190-29-3).
Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics