Dimethylformamide dimethyl acetal → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

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Reaction Conditions

Reaction Steps

DMF dimethyl acetal (5.82 ml, 0.044 mol) was added to a stirred solution of 1-boc-4-piperidone [Ashwood et al., J. Chem. Soc., Perkin 1, 641 (1995)] (8.73 g, 0.044 mol) in DMF (80 ml) and the reaction mixture was heated to 80° C. under N2 for 18 h. After cooling, the DMF was removed under reduced pressure and the residue was partitioned between EtOAc and H2O, the organic layer washed with H2O and saturated brine, then dried over MgSO4 and evaporated to afford the subtitle compound as a solid (8.44 g, 76%). Rf 0.33 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 255 (MH+).

Provenance & Evidence