Methanol → (R)-4-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)pentyl acetate

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask was combined 5-nitro-isochromen-1-one (5.50 g, 0.0259 mol), (R)-2-amino-4-methylpentan-1-ol (6.07 g, 0.0518 mol) and methanol (160 mL, 4.1 mol). The mixture was heated at reflux for 3 hours. The mixture was allowed to cool, reduced in vacuo and dried on high vacuum for approximately 1 hour. methylene chloride (200 mL, 3 mol) and acetyl chloride (4.1 g, 0.052 mol) were added and the mixture was heated at 50° C. for 3 hours. The resulting solution was reduced in vacuo and purified. The mixture was purified by column chromatography using a methanol:methylene chloride (0-3%) gradient. The combined pure fractions were reduced in vacuo to yield the title compound as a dark yellow solid which was taken to the next step without further purification.

Provenance & Evidence