(1-Boc-1,2,5,6-tetrahydropyridin-3-YL)methanol → tert-butyl 5-formyl-3,6-dihydro-1(2H)-pyridinecarboxylate
Reaction equation
[OH:1][CH2:2][C:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4]=1)=[O:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of tert-butyl 5-(hydroxymethyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (14.65 g, 68.69 mmol) in dichloromethane was added MnO2(89.58 g, 1030.36 mmol), then stirred overnight at room temperature. The reaction mixture was filtered through Celite®, the filtrate was concentrated under reduced pressure to give tert-butyl 5-formyl-3,6-dihydro-1(2H)-pyridinecarboxylate, which was pure enough to be used for the next reaction. (13.55 g, yield 94%)