A common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 103146-25-4.
Example 2 (Preparation of the mixture used in example 1) (S)-4-[4-Dimethylamino-1-(4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethyl- benzonitrile To a stirred solution of racemic 4- [4-Dimethylamino-l- (4-fluorophenyl)-l-hydroxy- butyl] -3-hydroxymethylbenzonitrile (29 mmol, 10 g) and vinylbutyrate (58 mmol, 7,5 ml) in anhydrous 1,4-dioxane (142,5 ml) is added lipoprotein lipase pseudomonas sp. (160 U, 250 mg). The reaction is heated to 50 C and followed by HPLC. After 192 hours at a conversion of 41%, additional 250 mg lipase was added. After 504 hours, at a conversion of 63 % the reaction was stopped. The enzyme is filtered off and washed with a small amount of 1,4-dioxane. The combined organic phases are evaporated in vacuo and subsequently analyzed on super critical fluid chromatography. Obtained ee-value ( (S-diol) = 95% (S-diol/R-diol = 40: 1).
The synthetic route of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; H. LUNDBECK A/S; WO2005/77891; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts