10049-64-6

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-(+)-3-Hydroxymandelonitrile is used as a key intermediate in the synthesis of various medications. Its chiral nature allows for the creation of enantiomerically pure compounds, which is crucial for the development of effective and safe pharmaceuticals.
Used in Agrochemical Synthesis:
In the agrochemical industry, (R)-(+)-3-Hydroxymandelonitrile is utilized as a building block for the development of new and improved agrochemicals. Its unique properties contribute to the creation of more effective and targeted products for agricultural applications.
Used in Organic Synthesis:
(R)-(+)-3-Hydroxymandelonitrile is employed as a versatile building block in organic synthesis, enabling the creation of a wide range of organic compounds with diverse applications. Its reactivity and structural features make it a valuable component in the synthesis of complex organic molecules.
Used in the Development of New Synthetic Methods:
(R)-(+)-3-Hydroxymandelonitrile has been studied for its potential in the development of innovative synthetic methods. Its unique properties and reactivity offer opportunities for the creation of new synthetic pathways, leading to more efficient and selective chemical reactions.

Upstream product

• 74-90-8 hydrogen cyanide 
• 100-83-4 meta-hydroxybenzaldehyde 

Relevant academic research and scientific papers

Synthesis of the Adrenergic Bronchodilators (R)-Terbutalinel and (R)-Salbutamol from (R)-Cyanohydrins

Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9·HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of (A)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (A)-7b and c to (R)-salbutamol was not yet possible without racemization.

Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes

A range of aryl, alkyl and heterocyclic aldehydes have been treated with hydrogen cyanide in the presence of the 'Inoue' catalyst, (R,R)- or (S,S)-cyclo.Most aryl aldehydes with electron-donating substituents in the m-or p-positions give high enantiomeric excess (e.e) values (>=80percent) but aryl aldehydes with strong electron-withdrawing substituents gave moderate e.e. values (=50percent).These moderate values are believed to be due to partial racemization of the product cyanohydrins in the presence of the mildly basic catalyst.In contrast to the reactions of aryl aldehydes, reactions of alkyl aldehydes and of ketones gave low e.e. values (=30percent) and an explanation is proposed.