Water → 1,1-Dimethylethyl (1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-3-hydroxypropyl}-4-piperidinyl)carbamate

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Reaction Conditions

Reaction Steps

A solution of methyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate (26.63 g, containing about 9% DMF by weight, estimate 52.5 mmol) was stirred under argon at −70° C. and treated with a 1M solution of lithium aluminium hydride in THF (60 ml). The mixture was allowed to warm to −10° C., stirred in an ice bath for 2 hours, treated with water (4.5 ml), 2N NaOH solution (8.44 ml) and water (9.7 ml) and stirred a further 30 minutes. The solid was filtered off and washed with THF and the filtrate evaporated. Chromatography of the residue (methanol/dichloromethane gradient) gave the product (18.28 g).

Provenance & Evidence