The Synthetic Routes of Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate is an important intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other chemical products.
The demand for this intermediate has been increasing steadily in recent years, making it an important subject for the chemical industry.
In this article, we will discuss the synthetic routes of methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate.

1. The classic route: The classical synthetic route for methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate involves the following steps:

a.
Ethyl 3-hydroxy-2-oxo-1,4-dihydro-pyridine-5-carboxylate: The synthesis of ethyl 3-hydroxy-2-oxo-1,4-dihydro-pyridine-5-carboxylate begins with the reaction of 2,2-dihydroxyethylamine with ethyl chloroformate.
The product is then treated with sodium hydroxide to achieve the desired pH and then stirred for several hours to allow for complete conversion of the starting material.

b.
3-(Benzyloxy)-1,4-dihydro-2H-pyridino[1,2-d][1,4]benzoxazepine-9-one: The next step involves the synthesis of 3-(benzyloxy)-1,4-dihydro-2H-pyridino[1,2-d][1,4]benzoxazepine-9-one using the traditional route, which involves several steps and reagents.
The reaction involves the treatment of ethyl 3-hydroxy-2-oxo-1,4-dihydro-pyridine-5-carboxylate with several reagents, such as benzyl bromide, sodium sulfate, and sodium hydroxide, followed by purification of the product using column chromatography.

c.
Methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate: The final step involves the synthesis of methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate.
This involves the treatment of 3-(benzyloxy)-1,4-dihydro-2H-pyridino[1,2-d][1,4]benzoxazepine-9-one with sodium hydroxide, followed by the addition of methyl iodide and sodium hydroxide.
The product is then purified using column chromatography.

2. The one-pot route: The one-pot synthetic route for methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate involves the following steps:

a.
Treatment of 2,2-dihydroxyethylamine with ethyl chloroformate: The synthesis of methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate begins with the reaction of 2,