Reacción #744062

Ecuación de reacción

NaBH(OAc)3

[7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde

1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate

NaHCO3

→

desired compound

Rendimiento 62.0%

1,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)(1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-4-piperidinyl)carbamate

Rendimiento 62.0%

Disolventes

MeOH

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe reaction was then extracted with 20% MeOH in DCM (3×200 ml)
2. 2
   OtroThe combined organic phases were dried
3. 3
   Otroevaporated
4. 4
   Otrothe crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient

Procedimiento

A mixture of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (530 mg, 2.431 mmol) and 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (for a synthesis see WO2004/058144 Example 99(h)) (848 mg, 2.431 mmol) in chloroform (20 ml) and MeOH (1 ml) was stirred for 2 h before addition of NaBH(OAc)3 (1.546 mg, 7.293 mmol). The reaction was stirred for 0.5 h before addition of sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the desired compound (833 mg, 62%).

Fuente