Acetic Acid → (R)-3-Amino-3-(6-methylpyridin-3-yl)propan-1-ol

HRID 241857

Reaction equation

HRID 241857 reaction equation
C([N:8]([C@H](C1C=CC=CC=1)C)[C@@H:9]([C:13]1[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=1)[CH2:10][CH2:11][OH:12])C1C=CC=CC=1.CC(O)=O.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@@H:9]([C:13]1[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=1)[CH2:10][CH2:11][OH:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723923Ammonium formateHCID 58103596(R)-3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propan-1-ol

Product 1

HCID 58103597(R)-3-Amino-3-(6-methylpyridin-3-yl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propan-1-ol (2.1 g, 5.83 mmol) in HPLC MeOH (40 mL), were added AcOH (0.34 mL, 5.8 mmol), Pd(OH)2 (0.42 g) and HCOONH4 (1.8 g, 29.16 mmol) and was heated to reflux. After 1 h, the reaction mixture was filtered through a Celite pad and the filtrate was concentrated in vacuo to afford a residue. Purification of the residue by column chromatography (neutral Al2O3, aq. NH3/MeOH/CH2Cl2, 1:20:80) afforded the title compound.

Workup

  1. temperaturewas heated to reflux
  2. filtrationthe reaction mixture was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto afford a residue
  5. customPurification of the residue by column chromatography (neutral Al2O3, aq. NH3/MeOH/CH2Cl2, 1:20:80)

Sources & evidence

ORD record
ord-3e222298bf52427ea59743fe661034b2
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Linked notes

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