Ethanol → Methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate

HRID 1713903Notes

Reaction equation

HRID 1713903 reaction equation
[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.CCO>[Pd].C1COCC1>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][C:2]([CH3:1])([C:17]([O:19][CH3:20])=[O:18])[CH2:3][CH2:4]2)=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 59464275Methyl 4-methyl-1-(5-nitropyridin-2-yl)piperidine-4-carboxylate

Product 1

HCID 59464146Methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-methyl-1-(5-nitropyridin-2-yl)piperidine-4-carboxylate (3.32 g, 11.89 mmol) in abs EtOH (200 mL) and THF (200 mL) was added 10% Pd/C (400 mg) and then the reaction mixture was evacuated with hydrogen (5 cycles) and allowed to stir at ambient temperature overnight. The reaction mixture was filtered and then concentrated and the black residue purified on a 120 g silica Crawford silicyle cartridge loading in 40% EtOAc/isohexane with some DCM and eluting a gradient of 40-80% EtOAc using an Isco companion to provide the title compound (2.96 g, 11.89 mmol, 100%).

Workup

  1. customthe reaction mixture was evacuated with hydrogen (5 cycles)
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customthe black residue purified on a 120 g silica Crawford silicyle cartridge loading in 40% EtOAc/isohexane with some DCM
  5. washeluting a gradient of 40-80% EtOAc using an Isco companion

Sources & evidence

ORD record
ord-4db8e991b6b148c78fb7e1806b1e112f
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…