Potassium Carbonate → Di-tert-butyl dicarbonate

HRID 481427Notes

Reaction equation

HRID 481427 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[C:12]([O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[CH3:2][O:3][C:4](=[O:11])[CH:5]1[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:6]1.[C:20]([O:19][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 187838294-Piperidinecarboxylic acid, methyl ester, hydrochloride (1:1)

Product 2

HCID 90495Di-tert-butyl dicarbonateHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isonipecotic acid methyl ester HCl (2-3b) (34 g, 0.19 mol), and di-tert-butyl dicarbonate (43.5 g, 0.2 mol) in THF (300 mL) and H2O (150 mL) was added-K2CO3 (28.8 g, 0.21 mol). After 4 hours, the mixture was poured into water, extracted with EtOAc then washed with brine, dried (MgSO4) and evaporated to give the title compound 2-3c as an oil with a small amount of di-tert-butyl dicarbonate.

Workup

  1. extractionextracted with EtOAc
  2. washthen washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-fc7ad82c9fb44272bc921a4008637bb6
Source dataset
uspto-grants-1998_08
Patent number
US05789421

Reaction notes

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