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

HRID 1698361Notes

Reaction equation

HRID 1698361 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), 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]+.

Workup

  1. temperatureat reflux overnight
  2. customThe MeOH is evaporated
  3. extractionthe residue extracted with dichloromethane 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-2255da03c43148c9adc17c1c80cf8fe6
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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