Ammonium formate → 3-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octane

HRID 1871912Notes

Reaction equation

HRID 1871912 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]([CH2:14][CH2:15]2)[CH:12]=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:17][CH:16]2[N:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 186899033-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene

Product 1

HCID 186899083-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octaneYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.0 gm (13.0 mMol) 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene, 0.5 gm 10% palladium on carbon and 8.22 gm (130 mMol) ammonium formate in 100 mL ethanol was stirred at room temperature for 16 hours and then at reflux for 1.5 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide 2.83 gm (70.4%) of 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo-[3.2.1]octane.

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b8e2e1765794a08b3cfb2001f8c34f4
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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