20804-76-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-4-(1-naphthyloxy)butyronitrile is used as a key intermediate in the synthesis of Nadoxolol (N201040) for its role as a beta-adrenergic receptor blocker. This application is crucial because Nadoxolol has potential therapeutic uses, particularly in managing conditions that involve the adrenergic system, such as hypertension and certain cardiac conditions. 3-hydroxy-4-(1-naphthyloxy)butyronitrile's role in the synthesis process is essential for creating a final product that can be used to treat these medical conditions effectively.

InChI:InChI=1/C14H13NO2/c15-9-8-12(16)10-17-14-7-3-5-11-4-1-2-6-13(11)14/h1-7,12,16H,8,10H2

Upstream product

• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 143-33-9 sodium cyanide 
• 20133-93-1 1-chloro-3-(1-naphthoxy)-2-propanol 
• 151-50-8 potassium cyanide 

Relevant academic research and scientific papers

New chemoenzymatic pathway for β-adrenergic blocking agents

The lipase mediated kinetic resolution of pharmaceutically important β-hydroxy nitriles is described in high enantiomeric excesses and good yields. Some of the chiral β-hydroxy nitriles have been employed in the synthesis of β-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-hydroxy-4-tosyloxybutanenitrile, chiral intermediates of high synthetic value.

Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols

An efficient kinetic resolution of racemic β-hydroxy nitriles 1 was performed via Candida antarctica lipase (N-435)-catalyzed transesterification. A variety of racemic alkyl, aryl, and aryloxymethyl substituted β-hydroxy nitriles was efficiently transformed to the corresponding enantiomerically pure acetates (ee > 99% and conversion = 50%) with E values from 40 to > 1000. The combination of the enzymatic kinetic resolution with a ruthenium-catalyzed alcohol racemization led to a dynamic kinetic resolution (ee's up to 99%, yields up to 85%).

A facile preparation of (±)-β-hydroxy nitriles and their enzymatic resolution with lipases

A simple and efficient method for the preparation of racemic 4-aryloxy-3-hydroxybutanenitriles is described. Lipase mediated kinetic resolution in organic media was then utilised to effect enantioseparation. Lipases from different sources were screened in the resolution reaction using a number of organic solvents. Enantiomeric excesses of up to 99% were obtained by employing lipase from Pseudomonas cepacia in di-iso-propyl ether medium.