Sodium periodate → Tert-butyl (1-(2-formylquinolin-8-yl)piperidin-4-yl)methylcarbamate
Reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][CH2:22]3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1)CO>C(Cl)Cl>[CH:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:23][CH2:22]3)[CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:7]Participants
4
Procedure
Sodium periodate (0.34 mL, 0.22 mmol was added drop-wise to a slurry of silica gel (0.4 g) in DCM (3 mL)). The reaction was stirred for 10 minutes. tert-Butyl (1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (74 mg, 0.18 mmol) in DCM (2 mL) was then added to the slurry and the reaction was stirred for 30 minutes. The reaction was filtered and the collected solids were washed with DCM (20 mL). The filtrate was concentrated to give the crude product.