(R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine → (R)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanamine

HRID 2071026Notes

Reaction equation

HRID 2071026 reaction equation
[N:1]([C@@H:4]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]([CH3:14])=[CH2:13])[CH:11]=1)[CH3:5])=[N+]=[N-]>CO.Cl.[Pd]>[CH2:13]=[C:12]([C:10]1[CH:11]=[C:6]([C@H:4]([NH2:1])[CH3:5])[CH:7]=[N:8][CH:9]=1)[CH3:14]

Participants

4

Reactant 1

HCID 86647423(R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine

Product 1

HCID 59569959(R)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanamineYield 83.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

To a stirred solution of (R)-3-(1-azidoethyl)-5-(prop-1-en-2-yl)pyridine (340 mg) in MeOH.HCl (1.25M, 10 mL) was added 10% Pd/C (50 mg) and stirred under hydrogen atmosphere for 12 h. The catalyst was filtered off and the residue was dissolved in 5 mL of 25% aqueous NH3 and extracted with CHCl3 and the organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (10% MeOH/90% CHCl3 spiked with 0.25% of Et3N) to provide 246 mg of (R)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanamine.

Workup

  1. filtrationThe catalyst was filtered off
  2. dissolutionthe residue was dissolved in 5 mL of 25% aqueous NH3
  3. extractionextracted with CHCl3
  4. washthe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (10% MeOH/90% CHCl3 spiked with 0.25% of Et3N)

Sources & evidence

ORD record
ord-69fe576fcbab4b2f8c941b9d504f4cda
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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