3-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene → 3-(2-Naphthyl)-8-azabicyclo[3.2.1]octane

HRID 987580Notes

Reaction equation

HRID 987580 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[NH:18][CH:13]([CH2:14][CH2:15]2)[CH:12]=1>CCOC(C)=O.[Pd]>[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[NH:18][CH:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

4

Reactant 1

HCID 119560113-(Naphth-2-yl)-8-azabicyclo[3.2.1]oct-2-ene

Product 1

HCID 180091773-(2-Naphthyl)-8-azabicyclo[3.2.1]octaneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 313 mg (1.33 mmol) 3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]oct-2-ene in 10 mL EtOAc is added 100 mg of 10% Pd/C. This mixture is placed under 40 psi of H2 and shaken in a Parr hydrogenator for 47 h. The resulting mixture is then filtered through celite and evaporated to give 197 mg (0.83 mmol, a 62% yield) of the title compound as a white solid. mp: 189-194° C.; MS (ES) m/z 238 (MH)+.

Workup

  1. filtrationThe resulting mixture is then filtered through celite
  2. customevaporated
  3. customto give 197 mg (0.83 mmol

Sources & evidence

ORD record
ord-cd82ecd92d614bcc9a672ccc1108eb8f
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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