4-[(1R)-1-Azidoethyl]pyridine → (R)-1-(4-Pyridyl)ethylamine

HRID 458400Notes

Reaction equation

HRID 458400 reaction equation
[N:1]([C@@H:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH3:5])=[N+]=[N-]>CCO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[N:9]1[CH:10]=[CH:11][C:6]([C@H:4]([NH2:1])[CH3:5])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 865981624-[(1R)-1-Azidoethyl]pyridine

Product 1

HCID 1084922(R)-1-(4-Pyridyl)ethylamineYield 71.3%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

4-[(1R)-1-Azidoethyl]pyridine (1.0 g, 6.7 mmol) was dissolved in 25 mL EtOH amd hydrogenated at 45 psi over 100 mg Lindlar's catalyst (5% w/w). After 2 h, the reaction mixture was filtered through Celite, concentrated and purified on SiO2 (DCM:MeOH:NH4OH 95:5:0.1) to provide the amine as a yellow oil (0.583 g, 4.78 mmol, 71%): 1H NMR (300 MHz, CDCl3) δ 8.44 (dd, J=4.5, 1.5 Hz, 2H), 7.34 (d, J=5.8 Hz, 2H), 3.93 (q, J=6.8 Hz, 1H), 3.3 (bs, 2H), 1.21 (d, J=6.5 Hz, 3H) ppm.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. custompurified on SiO2 (DCM:MeOH:NH4OH 95:5:0.1)

Sources & evidence

ORD record
ord-2cfb4d06f1634930b8c45bdf3e5fea9d
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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