Acetic Acid → N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

Participants

Reaction Conditions

Reaction Steps

N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide (Example 29(i)) (1.70 g) was dissolved in dichloromethane (50 mL), treated with acetic acid (1 mL) and cooled to −78° C. under nitrogen. Ozone was bubbled through the resulting solution for 2 hours while maintaining the temperature. Nitrogen was subsequently bubbled through the solution for 10 minutes and dimethylsulfide (2 mL) was added. The solution was warmed to room temperature washed with sodium bicarbonate (2×10 mL) and brine (30 mL); the organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20) to afford the sub-titled compound (1.13 g).

Provenance & Evidence