First Synthesis of <I>N</I>-(4-Fluorophenyl)-5-(4-fluorophenyl)-2-(4-hydroxybenzyl)pentanamide, a New Potential Cholesterol Absorption Inhibitor

Abstract

The ®rst synthesis of N-(4-¯uorophenyl)-5-(4-¯uorophenyl)-2-(4-hydroxybenzyl)pentanamide and a new synthesis of 1-(4-¯uorophenyl)-3-[(4-¯uorophenyl)propyl]-4-(4-hydroxyphenyl)-2-azetidinone starting from 4-¯uorobenzaldehyde are described. This new amide could represent a potential new cholesterol absorption inhibitor.Correspondence: J. Guillon, Syntheval,

Kinetics and Mechanism of the Base-Catalyzed Rearrangement and Hydrolysis of Ezetimibe

“…First step: 4‐Benzyloxybenzyliden‐ N ‐(4‐fluorophenyl)imine (6.8 g, 22.3 mmol) was dissolved in dry toluene (40 mL) under an argon atmosphere at 80°C and tributylamine was added in one portion. Then, a solution of propionyl chloride (2.1 g, 22.5 mmol) in toluene (40 mL) was added dropwise during 30 min, and the reaction mixture was stirred for 2 days at 80°C.…”