4-Methoxybenzylamine → 5-(4-Chloro-2-methyl-phenyl)-3-hydroxy-4-isobutyryl-1-(4-methoxy-benzyl)-1,5-dihydro-pyrrol-2-one

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Reaction Steps

5-Methyl-2,4-dioxo-hexanoic acid ethyl ester (5.6 g, 36.4 mmol) was added to a solution of 4-methoxybenzyl amine (5 g, 36.4 mmol) in acetic acid (40 mL). The mixture was stirred for 10 min at rt. 4-Chloro-2-methylbenzaldehyde (6.77 g, 36.4 mmol) was added. The reaction mixture was heated to 120° C., stirred at this temperature overnight, allowed to cool to rt and diluted with acetonitrile. The resulting precipitate was collected by vacuum filtration and dried to provide 11 g of the title compound. tR: 1.80 min (LC-MS 2); ESI-MS: 414 [M+H]+ (LC-MS 2).

Provenance & Evidence