Potassium Carbonate → 1-(Tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid
Reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH:9]([C:11]([O:13]C)=[O:12])[CH2:8][N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+]>CO.O>[C:18]([O:17][C:15]([N:7]1[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]Participants
4
Procedure
To a solution of piperidine-1,3,5-tricarboxylic acid 1-tert-butyl ester 3,5-dimethyl ester (6.8 g, 22.5 mmol) in MeOH/water (4:1, 120 mL), K2CO3 (9.4 g, 68 mmol) is added. The reaction is stirred at reflux overnight. The MeOH is evaporated and the residue extracted with dichloromethane and 1N aq. HCl. The organic phase is dried over Na2SO4, filtered and evaporated to give a light yellow solid. MS (LC-MS): 274 [M+H]+.