184763-87-9

Upstream product

• 110-89-4 piperidine 

Downstream Products

• 184764-41-8 [2-((2R,4R,6S)-6-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-phenyl-[1,3]dioxan-4-yl)-phenyl]-piperidin-1-yl-methanone 
• 184763-93-7 [2-((2R,4S,6S)-6-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-phenyl-[1,3]dioxan-4-yl)-phenyl]-piperidin-1-yl-methanone 

Relevant academic research and scientific papers

Synthesis of Montelukast (MK-0476) metabolic oxidation products

We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.