Fibrane the reduced derivative of fenofibrate

Kotheimer, Amanda E.; Haq, W.; Balendiran, Ganesaratnam K.

doi:10.1016/j.rechem.2019.100018

Cited by 1 publication

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“…Herein we report a facile and chemoselective reduction of a carboxylic group, more challenging carbonyl group, to corresponding alcohol in presence of a ketone under mild condition without any external ligand or catalyst in excellent yield and selectivity. In our ongoing research project on Fibrates we envisaged the synthesis of alcohol derivatives(4-chlorophenyl)(4-((1-hydroxy-2-methylpropan-2-yl) oxy)phenyl)methanone ( 3 ) [ 26 ] [ 27 ] [ 28 ]. The synthesis of the title compound can be achieved by the two step reaction as reported recently that involves double hydride reduction of the Fenofibrate, an agent against diabetes and that lowers lipid levels [ 29 ] [ 30 ] [ 31 ] [ 32 ] [ 33 ].…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Reduction of Fenofibric Acid to Alcohol in the Presence of Ketone by Mixed Anhydride and Sodium Borohydride

Majethia¹,

Haq²,

Balendiran³

2022

IJOC

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A highly efficient and facile protocol for the selective reduction of carboxylic acid of Fenofibric acid to corresponding alcohol was developed. The selective reduction was carried out by activation of carboxylic acid by mixed anhydride followed by the reaction of sodium borohydride in presence of methanol. This is the first example of chemoselective reduction of carboxylic acid to alcohol in presence of a ketone without any external catalyst or ligand in a single step. The reaction offers wide applicability for the selective carboxylic group reduction methodology. The chemoselective reduction was demonstrated by the reduction of Fenofibric acid, an active metabolite of the drug Fenofibrate, to corresponding alcohol in excellent selectivity, yield, and purity.

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