Ethyl 3-(6-acetylamino-pyrid-3-yl)-but-2-enoate → (RS) ethyl 3-(6-acetylamino-pyrid-3-yl)-butanoate

Reaction equation

[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]([CH3:18])=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Procedure

A solution of (E/Z) ethyl 3-(6-acetylamino-pyrid-3yl)-but-2-enoate (27.3 g, Reference Example 22) in ethanol (500 mL) was hydrogenated (3bar hydrogen pressure) at 50° C. using 10% palladium on charcoal (1.0 g) as catalyst. After 48 h, the mixture was degassed, filtered through a pad of diatomaceous earth and the pad rinsed through with ethanol. The filtrate was evaporated to give the title compound as an oil.