Potassium Carbonate → tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

HRID 18072

Reaction equation

HRID 18072 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH:15]C(=O)C(F)(F)F)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86593667(S)-2-[(2,2,2-Trifluoro-ethanoylamino)-methyl]-piperidine-1-carboxylic acid tert butyl ester

Product 1

HCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylateYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-[(2,2,2-Trifluoro-ethanoylamino)-methyl]-piperidine-1-carboxylic acid tert butyl ester (18.2 g) was dissolved in methanol (500 ml) and treated with potassium carbonate (16.1 g). After stirring for 16 h solvent was removed at reduced pressure and the residue partitioned between dichloromethane/water. The organic phase was separated, washed with brine, dried and solvent removed at reduced pressure. the residue was column chromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant) to give the title compound (8.82 g) of description 1.

Workup

  1. customwas removed at reduced pressure
  2. customthe residue partitioned between dichloromethane/water
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customdried
  6. customsolvent removed at reduced pressure
  7. customchromatographed (silica gel, 0-10% (9:1 methanol/ammonia) in dichloromethane eluant)

Sources & evidence

ORD record
ord-574a572bb7b6440f81d6cca69217e8a1
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Linked notes

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