Potassium Carbonate → 1-(Tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid

HRID 390378Notes

Reaction equation

HRID 390378 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

Reactant 2

HCID 11430Potassium CarbonateHCID 497610141-Tert-butyl 3,5-dimethyl piperidine-1,3,5-tricarboxylate

Product 1

HCID 232911311-(Tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

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) is added K2CO3 (9.4 g, 68 mmol). The reaction mixture is stirred at reflux overnight. The MeOH is evaporated and the residue is extracted with dicholoromethane 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]+.

Workup

  1. temperatureat reflux overnight
  2. customThe MeOH is evaporated
  3. extractionthe residue is extracted with dicholoromethane and 1N aq. HCl
  4. dry with materialThe organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a light yellow solid

Sources & evidence

ORD record
ord-24ab8030c61844feabb98b4269ff463e
Source dataset
uspto-grants-2013_02
Patent number
US08383650B2

Reaction notes

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