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

HRID 522865Notes

Reaction equation

[CH3:1][N:2]([CH:4](OC)OC)[CH3:3].[O:9]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1>CN(C=O)C>[CH3:1][N:2]([CH:4]=[C:15]1[C:10](=[O:9])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14]1)[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

DMF dimethyl acetal (5.82 mL, 0.044 mol) was added to a stirred solution of tert-butyl 4-oxopiperidine-1-carboxylate (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 was washed with H2O and saturated brine, then dried over MgSO4 and evaporated to afford tert-butyl 3-((dimethylamino)methylene)-4-oxopiperidine-1-carboxylate (8.44 g, 76%).

Workup

temperatureAfter cooling
customthe DMF was removed under reduced pressure
customthe residue was partitioned between EtOAc and H2O
washThe organic layer was washed with H2O and saturated brine
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-24c435952cd441cea073367e5e17047c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

Loading…