Ethanol → Undecane

HRID 15379Notes

Reaction equation

HRID 15379 reaction equation
N1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH:12]2N3[CH2:18][CH2:19][CH:14](C(=O)C3)[CH2:13]2)C[N+]([O-])=O)C=1.[CH2:21](O)C>[Ni]>[CH3:21][CH2:18][CH2:19][CH2:14][CH2:13][CH2:12][CH2:7][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 702EthanolHCID 684440356-(1-(3-Pyridinyl)-2-nitroethyl)-1-azabicyclo[2.2.2]octan-3-one

Product 1

HCID 14257UndecaneYield 67%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

6-(1-(3-Pyridinyl)-2-nitroethyl)-1-azabicyclo[2.2.2]octan-3-one (14.0 g, 0.046 mol) was dissolved in ethanol (200 mL), and then Raney nickel was added under nitrogen. The mixture was subjected to hydrogenolysis (40 psi H2) for 48 h and then filtered through Celite and concentrated by rotary evaporation to a crude brown residue. The residue was purified by column chromatography, using chloroform/methanol/ammonia (80:20:1, v/v) as eluent, to yield 3-pyridin-3-yl-1,5-diazatricyclo[5.2.2.0<2,6>]undecane as a yellow oil (8.0 g, 67%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated by rotary evaporation to a crude brown residue
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4102209460c747a59af0ecd015e21766
Source dataset
uspto-grants-2010_06
Patent number
US07732607B2

Reaction notes

Loading…