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

To a solution of methyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate (1.70 g, 3.83 mmol) in tetrahydrofuran (40 ml) at −78° C. was added lithium aluminium hydride (1M in diethyl ether, 4.59 ml, 4.59 mmol). The reaction was then stirred at −78° C. for 0.5 h before water (10 ml), then 2M NaOH solution (10 ml) and finally water (10 ml) was added and the mixture warmed to ambient temperature and then filtered and evaporated. The residue was subjected to column chromatography on silica gel using a 0-5% methanol in dichloromethane gradient affording the desired compound as a white solid (601 mg, 38%).

1. filtrationfiltered
2. customevaporated

ORD-Eintrag

ord-e079338607164a9eac2bc15c19164b47

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07732461B2