Ethanol → HCID 23565311, compound

HRID 1059288Notes

Reaction equation

HRID 1059288 reaction equation
C1S[C:4]([C:6]23[C:14](=O)[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][N:8]([CH3:16])[CH:7]3CC)([O-:5])SC1.[CH2:20]([OH:22])[CH3:21]>[Ni]>[CH2:20]([O:22][C:4]([C:6]12[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH2:9][N:8]([CH3:16])[CH2:7]2)=[O:5])[CH3:21]

Participants

4

Reactant 2

HCID 702EthanolHCID 86592273HCID 86592273, compound

Product 1

HCID 23565311HCID 23565311, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

2.42 g of ethyl(3-methyl-9-oxo-3-azabicyclo[3.3.1]non-1-yl)carboxylate ethylenedithioketal was dissolved in ethanol (200 ml). After adding 40 g of Raney nickel, the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluted with toluene/ethyl acetate) to thereby give 0.95 g of the title compound as a slightly yellow oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThen the reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluted with toluene/ethyl acetate)

Sources & evidence

ORD record
ord-c0bd1c1517044bcfa09e31caeabd14f8
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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