Benzyl 4-((tert-butoxycarbonyl)(methyl)amino)piperidine-1-carboxylate → 4-N-Boc-4-N-Methyl-aminopiperidine

HRID 2354071Notes

Reaction equation

HRID 2354071 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[C:22]([O:21][C:19](=[O:20])[N:17]([CH3:18])[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 1

HCID 20782499Benzyl 4-((tert-butoxycarbonyl)(methyl)amino)piperidine-1-carboxylate

Product 1

HCID 27568064-N-Boc-4-N-Methyl-aminopiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(tert-butoxycarbonyl-methyl-amino)-piperidine-1-carboxylic acid benzyl ester (17.5 mmol) and Pd—C (10%, 500 mg) in MeOH (150 mL) hydrogenated at atm. pressure and r.t. for 15 h. The mixture is filtered and evaporated. The residue is dissolved in CH2Cl2 (100 mL) and 1 M aq. NaOH (50 mL) is added. The mixture is stirred for 6 h at r.t., then the phases are separated and the aq. phase is extracted with CH2Cl2 (3×50 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated to provide the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. dissolutionThe residue is dissolved in CH2Cl2 (100 mL)
  4. addition1 M aq. NaOH (50 mL) is added
  5. customthe phases are separated
  6. extractionthe aq. phase is extracted with CH2Cl2 (3×50 mL)
  7. dry with materialThe combined organic extracts are dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-a68a6ca851604ecaaecb05539ba0318f
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

Loading…